The House has approved two tax bills that are part of Republicans’ three-pronged "Tax Reform 2.0" package. The two measures, approved by the House on September 27, focus on retirement savings and business innovation.

The House has approved two tax bills that are part of Republicans’ three-pronged "Tax Reform 2.0" package. The two measures, approved by the House on September 27, focus on retirement savings and business innovation.

The most controversial bill of the package, which would make permanent tax reform’s individual and small business tax cuts enacted last December, was approved by the House on September 28 (see the following story in this Issue). At this time, the Senate is neither expected to vote on the Tax Reform package before midterm elections in November nor approve the Tax Reform 2.0 package in its entirety.

Tax Reform 2.0
The Tax Reform 2.0 package was approved by the House Way and Means Committee on September 13. The following three bills are included in the package:

• Protecting Family and Small Business Tax Cuts Act of 2018 (HR 6760);
• Family Savings Act of 2018 (HR 6757); and
• American Innovation Act of 2018 (HR 6756).

The House approved HR 6757 on September 27 by a 240-to-177 vote. HR 6756 was approved minutes later by a 260-to-156 vote.

Savings Accounts
HR 6757 proposes an expansion of certain savings incentives. Among other things, the bill would eliminate the age limit on individual retirement account (IRA) contributions. Additionally, it would create a Universal Savings Account (USA) to which individuals could contribute up to $2,500 annually. Withdrawals from USA accounts would be tax free. Tax-advantaged funds in USA accounts could be used for purposes other than retirement. Also, the bill would expand Code Sec. 529 plans to permit use for expenses related to trade schools, home schooling, and up to $10,000 in total distributions for student loan repayment.

Business Innovation
HR 6756 would improve the tax treatment of certain start-up business expenses. The bill would allow new businesses to write off up to $20,000 of start-up and organization expenditures. Additionally, HR 6756 would allow for a change in start-up ownership without triggering limits on certain tax benefits.

Democratic Criticism
Democrats remain united in their opposition of Republicans’ Tax Reform 2.0 efforts. The lack of Democratic support makes the package’s success in the Senate, at least in current form, highly unlikely.

At least 60 Democratic votes would be needed for approval. Senate Majority Leader Mitch McConnell, R-Ky., has said that the Senate will not take up any bills in the package until the requisite votes are accounted for.

Specifically, Democrats criticize HR 6760 for extending TCJA provisions, a law that Democrats claim primarily benefits wealthy individuals and corporations. However, some Democratic support is expected in the Senate on the business innovation bill, HR 6756. There is talk on Capitol Hill that the bill could be approved by Congress in the lame duck session toward the end of the year.

White House
The Trump administration announced its support of the Tax Reform 2.0 package in a September 26 Statement of Administration Policy. The White House praised HR 6760 for "preventing a tax increase on millions of middle-income families and small businesses after 2025." Additionally, the Trump administration praised HR 6757, saying it would "assist start-up companies and entrepreneurs by allowing them to write off more costs associated with starting their new business and by allowing them to raise capital and expand without losing their previously accrued tax benefits."

The House has approved a tax bill that would make permanent tax reform’s individual and small business tax cuts enacted last December. The controversial bill is part of Republican’s three-bill "Tax Reform 2.0" package, two of which cleared the House on September 27 (see the previous story in this Issue).

The House has approved a tax bill that would make permanent tax reform’s individual and small business tax cuts enacted last December. The controversial bill is part of Republican’s three-bill "Tax Reform 2.0" package, two of which cleared the House on September 27 (see the previous story in this Issue).

Individual, Small Business Tax Cuts
The House approved the Protecting Family and Small Business Tax Cuts Act of 2018 (HR 6760) on September 28 by a 220-to-191 vote. The bill would make permanent certain individual and small business tax cuts enacted under the Tax Cuts and Jobs Act (TCJA) ( P.L. 115-97).

HR 6760 would make permanent certain TCJA individual tax cuts that are set to expire after 2025. These TCJA provisions were made temporary to comply with certain Senate budget rules applicable to the reconciliation process requiring only a simply GOP majority. Notably, these provisions include, among others:

• lower individual tax rates;
• a larger standard deduction;
• a $10,000 annual cap on the state and local tax (SALT) deduction; and
• a 20 percent deduction of business income for certain passthrough entities.

HR 6760 would reduce federal revenue by $631 billion over the next decade, according to a cost estimate by the nonpartisan Joint Committee on Taxation (JCT), (JCX-79-18). However, House Ways and Means Chairman Kevin Brady, R-Tex., highlighted the JCT’s findings particular to the bill’s macroeconomic effects. "Tax Reform 2.0 will permanently provide over $140 billion in annual tax relief for middle-class families, boost American GDP and investment, and create 1.1 million new jobs," Brady said in a statement, citing to the JCT report.

Democratic Support
Although the TCJA did not receive one Democratic vote, HR 6760, which extends many of the TCJA’s individual provisions, received three Democratic votes. Ten Republicans voted against the bill, all of whom hail from high-tax states and oppose the $10,000 annual cap on the SALT deduction.

Over 40 Democrats voted for the Family Savings Act of 2018 (HR 6757) and the American Innovation Act of 2018 (HR 6756), which focus on enhancing savings accounts and start-up business tax breaks. All three bills are now headed to the Senate, where the package is not expected to be considered before midterm elections in November. Additionally, the entire package is not expected to be approved by the Senate. However, it is considered likely on Capitol Hill that HR 6757, which promotes retirement and family savings, could be approved by the Senate in the lame-duck session.

"It’s encouraging to receive 44 Democratic votes in support of elements of Tax Reform 2.0," Brady said in a September 28 statement. "I’m confident that working with the Senate we can advance bipartisan bills to the President’s desk," he added.

Democratic Criticism
Although the Tax Reform 2.0 package did receive some Democratic support in the House, Democrats in both the House and Senate remain largely opposed to Republican efforts to extend the TCJA’s individual and small business tax cuts. Many Democrats have criticized the TCJA for primarily benefiting wealthy individuals and corporations.

"The Republicans’ tax 2.0 legislation is another reckless tax cut for the wealthy that leaves behind average, hardworking families," Ways and Means Committee ranking member, Richard Neal, D-Mass., said on the House floor just prior to the HR 6760 vote. "In less than a year, House Republicans have handed out trillions of tax cuts for the wealthy and big corporations," Neal added in a September 28 statement released after the 2.0 package cleared the chamber.

Meanwhile, House Speaker Paul Ryan, R-Wis., praised the Tax Reform 2.0 package for propelling economic growth and helping middle income taxpayers. "On top of making lower rates for individuals and small businesses permanent, these bills create new savings options for families to plan for education and retirement,"Ryan said in a September 28 statement.

Looking Ahead
House lawmakers left Washington, D.C. on September 28 to begin campaigning ahead of midterm elections in November. The Senate is not expected to take up the Tax Reform 2.0 package, if at all, until later this fall.

As for whether any of the three bills will become law this year, Brady remains optimistic. "We had 41 Democratic votes in support of retirement savings and that innovation for start-ups. I think that has a very good chance, with bipartisan support of getting to the President’s desk this year," Brady said in a September 28 televised interview. "The [individual tax cuts] permanency bill, that’s separate, will go to the Senate after today. [Senate Majority] Leader Mitch McConnell, has made it clear – when he sees a path for 60 votes, he’ll bring it forward."

Stakeholders are urging the IRS to clarify its guidance on tax reform’s new passthrough deduction. The IRS held an October 16 public hearing on proposed rules for the new Code Sec. 199Apassthrough deduction at its headquarters in Washington D.C. The IRS released the proposed regulations, REG-107892-18, on August 8.

Stakeholders are urging the IRS to clarify its guidance on tax reform’s new passthrough deduction. The IRS held an October 16 public hearing on proposed rules for the new Code Sec. 199Apassthrough deduction at its headquarters in Washington D.C. The IRS released the proposed regulations, REG-107892-18, on August 8.

Over 20 stakeholders and practitioners spoke at the hearing. Additionally, over 300 comments on the proposed rules have been submitted to Treasury and the IRS.

Passthrough Deduction
The new 20-percent deduction of qualified business income for passthrough entities, subject to certain limitations, was enacted as part of tax reform legislation last December. The Tax Cuts and Jobs Act ( P.L. 115-97) created the new Code Sec. 199A passthrough deduction for noncorporate taxpayers, effective for tax years beginning after December 31, 2017. The deduction is scheduled to sunset in 2026.

Rental Real Estate
Several speakers at the hearing asked the IRS for guidance clarifying whether rental real estate activities are eligible for the deduction. Additionally, Troy Lewis, testifying on behalf of the American Institute of Certified Professional Accountants (AICPA), asked the IRS for guidance on specific circumstances in which rental real estate activities would not produce qualified trade or business income pursuant to the adopted Code Sec. 162 standard.

"Without further guidance clarifying when the rental of real estate would fail to rise to the level of a section 162 trade or business, unnecessary ambiguity exists that will likely create a divergence in practice," the AICPA said in its written comments. "Taxpayers are thus left to pursue their own interpretation of the rules under section 199A and the IRS will likely face greater complexity of administration."

Likewise, the Council for Electronic Revenue Communication Advancement (CERCA) submitted comments highlighting the uncertainty as to whether and when a rental property is generally considered a qualifying trade or business for purposes of the Code Sec. 199A deduction. Notably, CERCA referenced the preamble to the regulations that indicates taxpayers should look to existing case law to determine whether rental activities meet the Code Sec. 162 standard. However, existing case law does not consistently apply a set of factors that taxpayers could reliably apply as rules, according to CERCA.

Determining that all rental real estate is a trade or business for purposes of the deduction would significantly simplify the deduction, Iona Harrison said, testifying on behalf of the National Association of Realtors. Making such a determination would also simplify IRS administration, she added.

SSTB
Several speakers and a number of comment letters requested that the IRS clarify its definition of a specified service trade or business (SSTB). The SSTB limitation is one of the most controversial provisions of the deduction. SSTBs are considered a "trade or business involving the performance of services in the fields of health, law, accounting, actuarial science, performing arts, consulting, athletics, financial services, investing and investment management, trading, dealing in certain assets or any trade or business where the principal asset is the reputation or skill of one or more of its employees," according to the IRS.

To that end, Major League Baseball (MLB) has pitched its assertion to the IRS that professional sports clubs are neither "personal services corporations" nor provide "services," as defined in Code Sec. 1202(e)(3)(A). The Office of the Commissioner of Baseball, which governs the 30 MLB clubs, has asserted in written comments that the business of a professional sports club is not an SSTB under Code Sec. 199A. Thus, "its owners should be allowed the full 199A deduction," Commissioner Robert D. Manfred, Jr. wrote in submitted comments.

Questions Remain
The October 16 public hearing served more as an opportunity for stakeholders to highlight issues rather than a forum for the IRS to provide answers. Treasury and the IRS are expected to consider hearing testimony and written comments when finalizing the rules. The regulations are expected to be finalized before the 2019 tax filing season.

Top Senate tax writers have introduced a bipartisan bill to prevent duplicative taxation on digital goods and services. The bill aims to establish a framework across multiple jurisdictions for taxation of digital goods and services, including electronic music, literature, and mobile apps, among other things.

Top Senate tax writers have introduced a bipartisan bill to prevent duplicative taxation on digital goods and services. The bill aims to establish a framework across multiple jurisdictions for taxation of digital goods and services, including electronic music, literature, and mobile apps, among other things.

The Digital Goods and Services Tax Fairness Act (Sen. 3581) was reintroduced on October 11 by Senate Finance Committee (SFC) ranking member Ron Wyden, D-Ore., and SFC member John Thune, R-S.D. A similar measure was previously introduced in 2015 by Thune and Wyden in the 114th Congress. A companion bill is expected to be reintroduced in the House.

Digital Marketplace
While the digital marketplace continues to evolve, federal law addressing taxation of digital goods and services "lags" behind, according to a joint press release issued by Thune and Wyden. "As a result, some consumers can be taxed multiple times on a single digitally delivered product or service by different tax jurisdictions," Thune said. "Our bipartisan legislation simply prevents this duplicative and discriminatory taxation, which will help ensure today’s digital economy isn’t held back unnecessarily and can continue to offer opportunities to entrepreneurs and consumers alike," Thune added.

"Preventing unfair taxes on music, books and other important goods and services benefits consumers and innovators alike," Wyden said. "This bipartisan legislation solves a 21st century tax riddle by establishing a comprehensive set of rules for states to follow."

The IRS has released Draft Instructions for the 2018 Form 1040. Additionally, the IRS has cautioned taxpayers that the draft instructions are subject to change. The IRS released a draft of the 2018 Form 1040 and six accompanying schedules last June.

The IRS has released Draft Instructions for the 2018 Form 1040. Additionally, the IRS has cautioned taxpayers that the draft instructions are subject to change. The IRS released a draft of the 2018 Form 1040 and six accompanying schedules last June.

Generally, the IRS does not release draft forms but has done so in this case as a "courtesy," the instructions state. "Do not rely on draft forms, instructions, and publications for filing,"the IRS wrote. Further, drafts of instructions and publications generally undergo some changes before being finalized, the IRS noted.

2018 Form 1040
Starting with the 2019 tax filing season, many taxpayers will be able to file federal income taxes on a new postcard-sized Form 1040. The IRS planned to finalize the new base 2018 Form 1040 this summer, an IRS spokesperson previously told Wolters Kluwer. "This early release is part of our standard process to invite stakeholder input into draft forms before finalizing them," the IRS spokesperson told Wolters Kluwer after the official release of the draft 2018 Form 1040.

Shorter Form, Six Schedules
The new, two-sided Form 1040 is intended to replace and consolidate current Forms 1040, 1040A and 1040EZ. "This new approach will simplify the 1040 so that all 150 million taxpayers can use the same form," the IRS said.

The shortened form reflects many of the changes to the tax code enacted under the Tax Cuts and Jobs Act (TCJA) ( P.L. 115-97). Some of these changes include the higher standard deduction and the elimination of certain deductions and personal exemptions. The new form now has 23 lines, decreased from 79. However, there are now six separate schedules that some taxpayers who continue to itemize will need to include with their return.

The IRS’s new Commissioner was officially sworn in on October 1 by Treasury Secretary Steven Mnuchin. IRS Commissioner Charles "Chuck" P. Rettig will lead the implementation of tax reform enacted last December under the Tax Cuts and Jobs Act (TCJA) ( P.L. 115-97).

The IRS’s new Commissioner was officially sworn in on October 1 by Treasury Secretary Steven Mnuchin. IRS Commissioner Charles "Chuck" P. Rettig will lead the implementation of tax reform enacted last December under the Tax Cuts and Jobs Act (TCJA) ( P.L. 115-97).

New IRS Commissioner
"I am honored, privileged and most humbled by the opportunity to serve with you as Commissioner," Rettig said in an internal IRS message obtained by Wolters Kluwer on October 2. "The foundation of my becoming Commissioner is a deep appreciation for the IRS, its workforce and our country."

The Senate confirmed Rettig’s nomination for IRS Commissioner by a 64-to-33 bipartisan vote. The Senate Finance Committee advanced Rettig’s nomination in July. President Donald Trump announced his nomination of Rettig last February.

IRS Priorities Moving Forward
Rettig outlined several IRS priorities in his message to IRS employees. Those priorities include, among others, implementing tax reform, balancing taxpayer service with tax enforcement, and deterring tax fraud.

"I know the Service has many challenges…I also know we must continue rebuilding trust with taxpayers while implementing the once-in-a-generation tax reform bill passed by Congress in December," Rettig said. "We must work on our IT modernization efforts," he added.

Additionally, while the IRS has been working toward moving more taxpayer services online, notably, Rettig emphasized the importance of providing personalized service to taxpayers. "Providing high-quality, personalized service is a critical component in helping taxpayers understand and comply with their filing and reporting obligations,"Rettig wrote.

Rettig’s term as the 49th IRS Commissioner is scheduled to expire on November 12, 2022. John Koskinen’s term as IRS Commissioner ended in November 2017. David Kautter, Assistant Secretary for Tax Policy at Treasury, has been serving as acting IRS Commissioner in the interim.

The Senate Small Business Committee held an October 3 hearing on expanding opportunities for small businesses through the tax code. Senate lawmakers examined tax reform’s effect on small businesses and discussed witnesses’ proposals to address ambiguity in the new tax code.

The Senate Small Business Committee held an October 3 hearing on expanding opportunities for small businesses through the tax code. Senate lawmakers examined tax reform’s effect on small businesses and discussed witnesses’ proposals to address ambiguity in the new tax code.

Various provisions of the Tax Cuts and Jobs Act (TCJA) ( P.L. 115-97) were discussed among lawmakers and witnesses. Specifically, Opportunity Zones under the TCJA were of particular focus.

Opportunity Zones
The TCJA created certain tax benefits for long-term business investment in Qualified Opportunity Zones, which generally include economically distressed communities. Although the TCJA did not receive a single Democratic vote, the Opportunity Zones program was generally based on a bipartisan bill sponsored by Sens. Tim Scott, R-S.C., and Cory Booker, D-N.J.

The TCJA’s Opportunity Zones program established tax incentives to spur business investment in these low-income communities to produce economic growth. Investor tax benefits include:

• a temporary tax deferral for capital gains reinvested in a qualified opportunity fund;
• the elimination of up to 15 percent of the tax on the capital gain that is invested in the qualified opportunity fund; and
• the potential for a permanent exclusion of tax when exiting a qualified opportunity fund investment.

"Opportunity Zones are the most innovative and ambitious federal attempt to encourage long-term private investment in low-income communities in at least a generation," John Lettieri, president and CEO of Economic Innovation Group, testified. However, "investors have yet to receive the formal guidance or regulatory clarity needed to inform their decision-making," he added.

Clarity/Reporting Metrics
Witnesses told lawmakers that definitional clarity and proper reporting metrics for the Opportunity Zone program are needed. Lettieri noted that Treasury has broad authority in determining Congressional intent for defining key terms pertaining to Qualified Opportunity Zone business and investment. "These rules must be designed with practical considerations and basic market flexibility in mind. If too narrow in scope or impractical in nature, the rules would undermine the very purpose for which this incentive was created," Lettieri testified.

Additionally, John Arensmeyer, founder and CEO of Small Business Majority, stressed the importance of measuring the program’s success. Those metrics should include evaluating success "based on the number of jobs created, where those jobs are located, employee wages and the number of businesses created, particularly businesses formed by women or people of color," Arensmeyer told lawmakers.

Treasury
Treasury Secretary Steven Mnuchin recently expressed his support for Opportunity Zones. "I couldn't be more excited about the opportunity zones," Mnuchin said in an interview last week. "I think there's going to be over $100 billion dollars in private capital that will be invested in opportunity zones," he added.

Comment. The Office of Management and Budget’s Office of Information and Regulatory Affairs (OIRA) is currently reviewing proposed IRS regulations on "Capital Gains Invested in Opportunity Zones."Generally, OIRA has 45 days to review proposed regulations but may expedite the process to 10 days for rules applicable to tax reform. According to the OIRA website, the proposed rule was submitted to OIRA on September 12, and the status of review is pending.

Taxpayers must generally provide documentation to support (or to “substantiate”) a claim for any contributions made to charity that they are planning to deduct from their income. Assuming that the contribution was made to a qualified organization, that the taxpayer has received either no benefit from the contribution or a benefit that was less than the value of the contribution, and that the taxpayer otherwise met the requirements for a qualified contribution, then taxpayers should worry next whether they have the proper records to prove their claim.

Taxpayers must generally provide documentation to support (or to “substantiate”) a claim for any contributions made to charity that they are planning to deduct from their income. Assuming that the contribution was made to a qualified organization, that the taxpayer has received either no benefit from the contribution or a benefit that was less than the value of the contribution, and that the taxpayer otherwise met the requirements for a qualified contribution, then taxpayers should worry next whether they have the proper records to prove their claim.

Cash donations

The taxpayer must provide records to prove a donation of any amount of cash (including payments by cash, check, electronic funds transfer or debit, and credit card). Acceptable records for cash donations of less than $250 generally include:

• An account statement or canceled check;
• A written letter, e-mail or other properly issued receipt from the qualified organization bearing the name of the organization and the date and amount of the contribution; and/or
• A pay stub, Form W–2, or other payroll document showing the amount of a contribution made from payroll.

Caution: A taxpayer cannot substantiate deductions through written records it has prepared on its own behalf, such as a checkbook or personal notes.

Cash donations of more than $250. If a taxpayer donated $250 or more in cash at any one time, the taxpayer must provide a contemporaneous written acknowledgment of the donation from the qualified organization. For each donation of $250 or more, the taxpayer must obtain a separate written acknowledgment. Furthermore, this written acknowledgement must:

• State the amount of the contribution; and
• State whether the qualified organization provided the taxpayer with any goods or services in exchange for the donation, and if so estimate their value; and
• Be received by the taxpayer before the earlier of (1) the return’s filing date or (2) the due date of the return, plus any extensions.

Note: The written acknowledgment ideally would also show the date of the contribution. If it does not, the taxpayer must also provide a bank record that indicates the date.

The acknowledgment must contain a statement of whether or not a taxpayer received any goods or services as a result of the donation, even if no goods or services were received. Even if the donation was for tithes to a religious organization, such as a church, synagogue, or mosque, the acknowledgment should state that the only goods and services received were of intangible religious value. The Tax Court has upheld the disallowance of charitable contribution deductions where the written acknowledgment omitted such a statement regarding goods or services provided.

Noncash contributions

As with cash contributions, the requirements for substantiating noncash contributions increase with the value of the contribution. For example, to substantiate noncash contributions of less than $250, taxpayers must show a receipt or other written communication from the charitable organizations.

To substantiate a noncash contribution between $250 and $500, the taxpayer must obtain a written acknowledgment of the contribution from the qualified organization prior to the earlier of the filing date or due date of its return. The acknowledgment must also describe the type and value of the goods and services, if any, provided to the taxpayer as a result of the donation.

To substantiate noncash contributions totaling between $500 and $5,000 or donations of publically traded securities, a taxpayer must complete Section A of Form 8283, Noncash Charitable Contributions. To substantiate noncash contributions of $5,000 or more (for example, donations of art, jewelry, vehicles, qualified conservation contributions, or intellectual property) the taxpayer must complete Section B of Form 8283. Generally, this would also require the taxpayer to obtain a qualified appraisal of the property’s fair market value.

A word about valuation. A charity is not obligated to provide a value to any noncash contribution; its written receipt only needs to describe the item(s) and note the date of the contribution. The taxpayer, however, is not relieved from making a good-faith estimate of value, which of course the IRS may dispute on any audit. “Thrift-shop” value is often used to value donations of clothing and household goods.

Caution: Last year the Treasury Inspector General for Tax Administration (TIGTA) issued a report finding that the IRS was not accurately monitoring the reporting of noncash contributions requiring completion of Form 8283. The IRS responded that it agreed that it needed to initiate more correspondence audits with taxpayers claiming noncash contributions without the necessary Form 8283 and appraisal.

Vehicles. A taxpayer who donates a motor vehicle, boat, or airplane to charity must deduct either the gross proceeds from the qualified organization’s sale of the vehicle or, if the vehicle is used within the charity’s mission, the fair market value of the vehicle on the date of the contribution, whichever is smaller. The taxpayer must also obtain and attach Form 1098-C, Contributions of Motor Vehicles, Boats, and Airplanes, to its return in addition to Form 8283.

The requirements for substantiating charitable contributions can be complicated. Please contact our office with questions.

Vacation homes offer owners many tax breaks similar to those for primary residences. Vacation homes also offer owners the opportunity to earn tax-advantaged and even tax-free income from a certain level of rental income. The value of vacation homes are also on the rise again, offering an investment side to ownership that can ultimately be realized at a beneficial long-term capital gains rate.

Vacation homes offer owners many tax breaks similar to those for primary residences. Vacation homes also offer owners the opportunity to earn tax-advantaged and even tax-free income from a certain level of rental income. The value of vacation homes are also on the rise again, offering an investment side to ownership that can ultimately be realized at a beneficial long-term capital gains rate.

Homeowners can deduct mortgage interest they pay on up to $1 million of "acquisition indebtedness" incurred to buy their primary residence and one additional residence. If their total mortgage indebtedness exceeds $1 million, they can still deduct the interest they pay on their first $1 million. If one mortgage carries a substantially higher rate than the second, it makes sense to deduct the higher interest first to maximize deductions.

Vacation homeowners don't need to buy an actual house (or even a condominium) to take advantage of second-home mortgage interest deductions. They can deduct interest they pay on a loan secured by a timeshare, yacht, or motor home so long as it includes sleeping, cooking, and toilet facilities.

Capital gain on vacation properties. Gains from selling a vacation home are generally taxed as long-term capital gains on Schedule D. As with a primary residence, basis includes the property's contract price (including any mortgage assumed or taken "subject to"), nondeductible closing costs (title insurance and fees, surveys and recording fees, transfer taxes, etc.), and improvements. "Adjusted proceeds" include the property's sale price, minus expenses of sale (real estate commissions, title fees, etc.). The maximum tax on capital gain is now 20 percent, with an additional 3.8 percent net investment tax depending upon income level. There's no separate exclusion that applies when selling a vacation home as there is up to $500,000 for a primary residence.

Vacation home rentals. Many vacation home owners rent those homes to draw income and help finance the cost of owning the home. These rentals are taxed under one of three sets of rules depending on how long the homeowner rents the property.

1. Income from rentals totaling not more than 14 days per year is nontaxable.
2. Income from rentals totaling more than 14 days per year is taxable and is generally reported on Schedule E of Form 1040. Homeowners who rent their properties for more than 14 days can deduct a portion of their mortgage interest, property taxes, maintenance, utilities, and other expenses to offset that income. That deduction depends on how many days they use the residence personally versus how many days they rent it.
3. Owners who use their home personally for less than 14 days and less than 10% of the total rental days can treat the property as true "rental" property, which entitled them to a greater number of deductions.