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Critical Tax Issues for Increasing Wealth

Author/Moderator: William R. Bischoff, MBA, CPA
Publisher: AICPA
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Description

Employ recent tax legislation changes to turn your older, wealthier and selfemployed tax clients into profitable financial planning clients. With fullycoordinated structuring techniques, you can increase your client’s cash flow and protect their assets while reducing income and estate taxes.

Focus on strategies that are only available to the self-employed. Look at the latest ideas in college funding. Help your older clients make the right decisions on retirement account contributions and distributions.

OBJECTIVES:

  • Use artful strategies for the self-employed
  • Implement state-of-the-art college financing strategies
  • Advise older clients on how to preserve wealth and transfer it to the next generation
  • Employ tax planning in the event of divorce
  • Take advantage of favorable estate tax rules
PREREQUISITE: Basic knowledge of individual financial planning and taxes

Accepted for PFS and EA credit.

Table of Contents


  • Chapter 1 - Top Tax-Saving Strategies for Small Business Owners
    • Learning Objectives
    • Introduction
    • Business Co-Owners Need Buy-Sell Agreements
      • Buy-Sell Agreement Basics
      • Redemption Agreements
      • Cross-Purchase Agreements
      • Hybrid Agreements
      • Funding Buy-Sell Agreement Obligations
      • Tax-Saving Provisions for Buy-Sell Agreements
      • Buy-Sell Agreements also Have Estate Planning Advantages
    • Sole Proprietors Can Hire Their Spouses and Save Taxes
      • Set Up Medical Reimbursement Plan
      • Mind the Details
    • Sole Proprietors Can Hire Their Kids and Save Taxes
    • Tax Savings from Work-Related Education Expenses
      • When Is Tax-Favored Treatment Available?
      • When Education Fails Tax-Law Standards
      • Deducting MBA Expenses
      • What about Undergraduate Degree Costs?
      • Remember Higher-Education Tax Credits and Tuition Deduction
    • Deduct College Tuition for Business Owner’s Child as Business Expense
      • Pass Section 127 Tests
      • Compound Tax Savings with Other Education Breaks
    • Deductions for Business Travel
      • Deduct Domestic Transportation Costs
      • Take Advantage of Saturday Night Stayover Rule
      • Deduct Foreign Travel Expenses
    • Consider Big Vehicles for Big Tax Savings
      • Reduced Section 179 Deduction for Heavy SUVs
      • Despite $25,000 Limitation, Depreciation Rules for Heavy SUVs Are Still Very Favorable
      • Do Not Forget Section 179 Taxable Income Limitation
      • Do Not Forget Section 179 Deduction Phase-Out Rule
      • Mind Stricter Rules for Corporate-Owned Vehicles
      • Bigger Section 179 Deduction for Tax Years Beginning in 2008
      • First-Year Bonus Depreciation Is Back (Temporarily)
      • Other Caveats
      • Plan Ahead to Preserve Client’s Section 179 Tax Savings for Heavy Business Vehicle
    • Deduction for Office in the Home
      • Home Office Used for Self-Employed Business
      • Home Office Used for Work as Employee
    • Claiming Gain Exclusion for Home Used Partly for Business
      • Treatment of Business Portion of Property
    • Health Savings Accounts
      • HSA Basics
      • Clients Can Rake in Major Tax Savings over the Years
      • Those 55 and Older Can Make Larger Contributions
      • Eligibility Rules
      • FSA/HRA Rollovers
      • IRA Rollovers
      • Employer-Funded HSAs
      • How to Set Up an HSA
      • Conclusion on HSAs
    • Summary
    • Question
  • Chapter 2 - Maximizing the Home Sale Gain Exclusion Privilege
    • Learning Objectives
    • Introduction
    • Home Sale Gain Exclusion Basics
    • What Qualifies as a Principal Residence?
    • Passing Ownership and Use Tests (or Not)
      • Co-Ownership by Unmarried Taxpayers
      • Claiming Exclusion on Joint Return
      • Claiming Exclusion after Spouse’s Death
      • Special Exception for Unmarried Surviving Spouses May Permit Larger $500,000 Gain
      • Exclusion
      • Periods of Ownership and Use Need Not Be Concurrent
    • Meeting the Anti-Recycling Rule (or Not)
    • Excluding Gain from Sale of Land Next to Residence
    • Claiming Reduced Exclusion for “Prematureâ€? Sales
      • Premature Sale Due to Employment Change
      • Premature Sale Due to Health Reasons
      • Premature Sale Due to Certain Unforeseen Circumstances
      • Premature Sales in Other Situations
      • Premature Sale of Property Used for Business or Rental
      • Reduced Gain Exclusion after Marriage
    • “Electing Outâ€? of Gain Exclusion
    • More Tax-Smart Home Sale Strategies
      • Rent Out Former Principal Residence and Claim Gain Exclusion Years Later
      • Swap Greatly Appreciated Residence for Income-Producing Property in Section 1031
      • Exchange
      • Combine Section 1031 Exchange with Gain Exclusion Break to Collect Tax-Free Cash
      • Hold Greatly Appreciated Home until Bitter End
    • Other Tax Planning Implications of the Gain Exclusion Privilege
    • Impact on Client Recordkeeping
    • Understanding the Tax Implications of Personal Residence Short Sales and Foreclosures and the
    • New Exclusion for Cancellation of Debt Income from Principal Residence Mortgages
      • Tax Rules for Cancellation of Debt Income
      • What If the Lender Forecloses?
      • New Exception for Principal Residence Mortgage Debt Discharges Will Save the Day for Many
      • Clients
    • Summary
  • Chapter 3 - State-of-the-Art College Saving and Financing Strategies
    • Learning Objectives
    • Introduction
    • Maximize Well-Known College Tax Breaks
      • Claim Hope Scholarship Credit
      • Claim Lifetime Learning Credit
      • Rules Applying to Both Credits
      • Beating the System
      • Write-Off College Tuition Costs
      • Deduct College Loan Interest
      • Contribute to Coverdell Education Savings Accounts (Formerly Education IRAs)
      • Tax-Free Employer Reimbursements for Higher Education Costs
      • Tax-Free U.S. Savings Bond Interest for College
      • Accrual Method for Savings Bonds Held by College-Bound Child
      • Penalty-Free IRA Withdrawals for Higher Education Costs
    • Tax-Smart College Financing Maneuvers for High-Income Clients
      • Section 529 Plans (Also Known as Qualified Tuition Programs)
      • Saving for College in Child’s (Student’s) Name May No Longer Be Inadvisable
      • Saving for College Using Parent’s Taxable Account
      • Saving for College Using Child’s Roth IRA
      • Make Direct Gifts to College for Tuition
    • Last-Minute College Financing Strategies
      • Take out Home Equity Loan
      • Gift Appreciated Assets; Sell Loss Assets
      • Borrow from Qualified Retirement Plan Account
    • Summary
  • Chapter 4 - Strategies for Divorcing Clients
    • Learning Objectives
    • Introduction
    • Tax Planning for Asset Transfers between Divorcing Clients
      • Splitting up Assets Held in Taxable Investment Accounts
      • Tax-Free Post-Divorce Transfers Must Be Incident to Divorce
      • Beware of Investments with Accrued Ordinary Income
    • Tax-Smart Divorce Strategies for Homes
      • Sale before Divorce
      • Sale in Year of Divorce or Later
      • When Nonresident Ex-Spouse Still Owns Home Long after Divorce
      • Vacation Homes
    • Splitting up Vested Employer Stock Options in Divorce
      • Federal Income and Gift Tax Consequences
      • Federal Employment Tax Consequences
    • Splitting up Business Ownership Interests in Divorce
      • Redemption of C Corporation Stock
    • Splitting up Tax-Advantaged Retirement Accounts in Divorce
      • How to Split up Qualified Retirement Plan Accounts
      • How to Split up Traditional IRAs, Roth IRAs, and SEP Accounts
      • Procedural Strategies for Traditional IRAs, Roth IRAs, and SEP Accounts
    • Structuring Payments to Qualify as Deductible Alimony
      • Tax-Law Requirements for Deductible Alimony
      • Written Instrument
      • Cash or Cash Equivalent
      • Payment to Third Parties
      • Requirement That Payments Must Cease after Payee’s Death
      • Payments Considered to Be for Child Support
      • Alimony Recapture Rules
    • Summary
    • Questions
  • Chapter 5 - Maximizing Retirement Plan Benefits
    • Learning Objectives
    • Introduction
    • Small Business Retirement Plan Basics
    • Solo or Family 401(k) Plan
    • Simplified Employee Pension (SEP)
      • SEP Pros
      • SEP Cons
      • Conclusion on SEPs
    • Defined Contribution Keogh and Corporate Profit-Sharing Plans
      • Pros for These Plans
      • Cons for These Plans
      • Conclusion on These Plans
    • SIMPLE-IRA
      • SIMPLE-IRA Pros
      • SIMPLE-IRA Cons
      • Conclusion on SIMPLE-IRAs
    • Defined Benefit Pension Plan
      • Defined Benefit Plan Pros
      • Defined Benefit Plan Cons
      • Conclusion on Defined Benefit Plans
    • Solo 401(k) Plan
      • Solo 401(k)’s Advantage Shrinks at High Income Levels
      • Solo 401(k) Mechanics
      • Solo 401(k) Pros
      • Solo 401(k) Cons
      • Conclusion Regarding Solo 401(k) Plans
    • Family 401(k) Plan When Business Owner Also Employs Other Family Members
      • Family 401(k) Mechanics
      • Family 401(k) Pros
      • Family 401(k) Cons
      • Conclusion on Family 401(k) Plans
    • Overall Conclusions on Small Business Retirement Plans
    • Planning for Retirement Account Rollovers
      • Avoid 20% Withholding Rule
      • Liberalized Rollover Rules
    • Appropriate Asset Allocation Strategies for Retirement Accounts
    • Impact of Rate of Return
      • Relationship between Investment Risk and Asset Allocation
      • Sample Asset Allocation Strategies
      • Laddered Approach to Asset Allocation
    • Sample Filled-Out Retirement Planning Worksheets
      • Worksheet No. 1: Projected Income from Current Retirement Savings plus Pension and Social
      • Security Benefits
      • Worksheet No. 2: Projected Retirement-Age Living Costs
      • Worksheet No. 3: Is Client Financially Set for Retirement or (More Likely) Are Additional Savings Required?
    • Summary
    • Question
  • Chapter 6 - How to Handle Retirement Account Required Minimum Withdrawals
    • Learning Objectives
    • Introduction
    • Part 1 – Required Minimum Withdrawals for Original Account Owners
      • Required Minimum Withdrawal Basics
      • Scenario 1: Account Owner Turns 70½ This Year; Takes First Required Minimum Withdrawal This Year
      • Scenario 2: Account Owner Turns 70½ This Year; Takes First Required Minimum Withdrawal Next Year
      • Scenario 3: Account Owner Turned 70½ Last Year; Took First Required Minimum Withdrawal Last Year
      • Scenario 4: Account Owner Turned 70½ Last Year; Takes First Required Minimum Withdrawal This Year
      • Scenario 5: Original Account Owner’s Much-Younger Spouse Is Named as Sole Account
      • Beneficiary
      • Scenario 6: Multiple IRAs
      • Qualified Charitable Distributions
    • Part 2 – Required Minimum Withdrawals When Surviving Spouse Inherits Account
      • Scenario 1: Spouse Dies before April 1st of Year after Turning 70½ (or Any Earlier Date)
      • Scenario 2: Spouse Dies on or after April 1st of Year after Turning 70½
      • Scenario 3: Surviving Spouse Inherits Roth IRA
      • Scenario 4: Estate or Trust Is Sole Account Beneficiary and Surviving Spouse Is Sole
    • Beneficiary of Estate or Trust
    • Part 3 – Required Minimum Withdrawals When Non-Spouse Inherits Account
      • Scenario 1: Account Owner Dies before April 1st of Year after Turning 70½ (or Any Earlier
      • Date)
      • Scenario 2: Account Owner Dies on or after April 1st of Year after Turning 70½
      • Scenario 3: Beneficiary Inherits Account from Original Account Owner’s Spouse
      • Non-Spousal Rollover Rules
    • Part 4 – Required Minimum Withdrawals in Special Circumstances
      • Scenario 1: No Designated Account Beneficiary
      • Scenario 2: Multiple Account Beneficiaries
      • Scenario 3: Beneficiary Wants to Disclaim Share of Inherited Account
      • Scenario 4: Removing a Non-Individual Beneficiary
    • Part 5 – The “Stretch IRAâ€? Strategy in Plain English
      • Stretch IRA Basics
      • The Stretch Roth IRA Strategy
    • Summary
    • Questions
  • Chapter 7 - Simple and Easy Estate Planning Strategies
    • Learning Objectives
    • Introduction
    • The Federal Gift and Estate Tax System in a Nutshell
      • Federal Estate Tax Basics
      • Federal Gift Tax Basics
      • Putting the Pieces Together
    • Estate Planning Basics
    • Step 1: Draft Will or Living Trust Instrument
      • The Will
      • The Living Trust
      • Wills and Living Trusts Are Not Cure-Alls
    • Step 2: Implement Estate-Tax-Avoidance Strategies
      • Use Will or Living Trust to Avoid Estate Tax Hit
      • Use Bypass Trust to Avoid Estate Tax Hit
      • Smaller Estates, Bigger Estates, and Singles
      • Use QTIP Trust to Avoid Estate Tax Hit
      • Use Life Insurance Trust to Avoid Estate Tax Hit
      • Use Marital Trust for Non-Tax Reasons
      • Estate Plans Are Moving Targets
    • Assessing Client's Estate Tax Exposure
    • Estate Planning with Roth IRAs
    • Estate Planning with Section 529 Accounts
    • Transferring Parent's Home to an Adult Child
      • Outright Gift of Home
      • Bargain Sale of Home
      • Full-Price Sale with Parental Financing
      • When Parent Wants to Continue Occupying the Home
      • Transfer to Qualified Personal Residence Trust
      • Post-Mortem Transfer Could Be Best Deal of All
    • Qualified Disclaimer Can Be Effective Estate Planning Tool
    • Summary
    • Questions
  • Chapter 8 - Ethics Focus: Taxation
    • Ethics Overview
    • Recent Developments
    • Spotlight on Independence in Tax Services
    • Key Ethical Dilemmas and Judgment Calls
    • Addressing Ethical Dilemmas
    • Available Resources
  • Chapter 9 - Latest Developments

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Excerpts

Chapter 1 - Top Tax-Saving Strategies for Small Business Owners

Learning Objectives

After completing this chapter, you should be able to

  • Explain the tax and non-tax advantages of buy-sell agreements to clients.
  • Understand why it is a tax-smart move for self-employed clients to hire their spouses and children.
  • Tell small business clients how to maximize deductions for education and travel costs.
  • Advise self-employed clients on tax-smart choices for vehicles used over 50% for business.
  • Understand the interaction between the home office deduction rules and the home sale gain exclusion rules.
  • Advise clients on setting up health savings accounts (HSAs).

Introduction

This chapter includes a selection of the best tax-saving breaks available to small business owners after recent tax-law changes and developments.

Business Co-Owners Need Buy-Sell Agreements

When the client is a business co-owner, he/she should almost certainly have a written buy-sell agreement in force. Why? Because the agreement can turn the client's closely held ownership interest into a much more liquid asset, prevent the entry of unwanted new owners, and deliver important tax advantages. Here is the story.

A buy-sell agreement is a contract between the co-owners or between each co-owner and the business entity. It has two main non-tax purposes:

  1. To limit the ability of existing co-owners to transfer ownership to anyone outside the current group, and
  2. To ensure there is a buyer for each co-owner's interest if and when he/she dies, retires, becomes disabled, etc.

Buy-Sell Agreement Basics

When certain events occur, the business ownership interest must be sold - or at least offered for sale - to the other co-owners and/or to the corporation, partnership, or LLC. The triggering events that will activate the agreement are specified in the document. These should include death, disability, and attainment of retirement age. Other triggering events (such as the desire of a co-owner to withdraw his/her equity from the business for whatever reason, loss of professional license, bankruptcy, and so forth) can also be listed to suit the preferences of the coowners.

The buy-sell agreement should specify a method to determine the price for the ownership interest and terms regarding how that amount will be paid out. Common methods include setting a fixed per-share price, using an appraised fair market value (FMV) price, or following a formula price based on a multiple of earnings, cash flow, or book value. Picking an appropriate valuation method involves assessing the nature of the business and its expected growth. As explained later, the price-setting method that is chosen should be one that will stand up to IRS scrutiny for estate tax purposes.

To the withdrawing owner, or heirs of a deceased owner, the buy-sell agreement represents a right of first refusal granted to the remaining owners or to the business entity (corporation, LLC, or partnership). If that right is not exercised, the withdrawing owner is typically free to sell his/her ownership interest to an outsider.

To the remaining owners - or the business entity - the agreement represents an obligation to buy out the withdrawing owner if a potential outside buyer is unacceptable or cannot be found.

Key Point. A buy-sell agreement guarantees there will be a market for the withdrawing owner's interest. It also guarantees the remaining owners will have control over who can join the party. This is a good deal for all concerned.

Depending on where the money for the buyout is coming from, a buy-sell agreement will fall into one of the following three categories:

  • Redemption Agreement.
  • Cross-Purchase Agreement.
  • Hybrid Agreement.

Redemption Agreements

Under a redemption agreement, the business entity itself (corporation, LLC, or partnership) is obligated to buy out the withdrawing (or deceased) owner.

For a C corporation business, a stock redemption can raise the challenge of avoiding dividend treatment for the redemption payments. Specifically, redemption payments are treated as dividends to the extent of the corporation's current or accumulated earnings and profits unless one of the exceptions under IRC Sec. 302(b) or 303(a) applies. [See IRC Secs. 301(c)(1), 302(b), 302(d), 303(a), and 317(b).]

Avoiding dividend treatment is usually possible as long as all of the withdrawing owner's stock is redeemed, including stock attributed to the withdrawing owner via his/her ownership of certain entities. [See IRC Sec. 302(b)(3), (b)(5), and (c).] When dividend treatment is successfully avoided, the redemption payments are treated as made in exchange for the withdrawing owner's stock, which means favorable capital gains treatment for him/her [IRC Sec. 302(a)].

How to Structure C Corp Stock Redemptions as Sales

With a redemption of C corporation stock, the federal income tax consequences depend on whether the corporate payments for the client's redeemed shares are treated as dividends or as proceeds from selling her stock. Before the Jobs and Growth Tax Relief Reconciliation Act of 2003, the client surely did not want dividend treatment, because dividends were taxed as ordinary income at rates of up to 38.6%. Now it may not matter. Or, it may still be important. Read on.

The exact federal income tax treatment for distributions (payments) from a C corporation to a shareholder to redeem some or all of the shareholder's stock depends on the amount of the corporation's current or accumulated earnings and profits (E&P).

  • Distributions up to the amount of a domestic corporation's E&P will generally count as qualified dividends eligible for the 15% rate (unless the redemption is treated as a sale, as explained later). Obviously, this is no longer a horrible result, thanks to the preferential tax rates on qualified dividends.
  • Distributions in excess of E&P go first to reduce the shareholder's tax basis in her stock (i.e., she receives these amounts free of tax).
  • Any distribution in excess of stock basis is treated as capital gain (i.e., it will generally be taxed at the 15% maximum rate for long-term capital gains). [See IRC Secs. 301(c), 312, and 316(a).]

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Videocourse Details

NASBA Field of Study: Taxes
Level: Intermediate
Recommended CPE Credit: 16
Tax Planning
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