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Innovative Tax Planning for Small Businesses: Corporations, Partnerships & LLCs

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

This fast-paced, information-packed program showcases state-of-the-art planning ideas and tax-saving devices to show you how to keep more profits in the pockets of corporate clients and business owners. And, all with an emphasis on the current year’s returns. This course helps you offer clients quality service.

Objectives:
  • Solve the unique tax problems affecting small businesses
  • Identify savings opportunities and pinpoint tax traps
  • Explain changes in each client’s tax situation
  • Substantially cut small business clients’ tax bills

Prerequisite:  Basic knowledge of corporate income taxation.

Table of Contents

  • Chapter 0 - Overview
    • Course Goals
    • Introduction
    • Conclusion
  • Chapter 1 - Corporate Tax Trends
    • Learning Objectives
    • Introduction
    • Taking Advantage of Planning Strategies Under the Current Tax Rate Structure (Before It Ends)
      • Current Strategies for Closely Held C Corps
    • INDOPCO Trends
      • Implications
      • INDOPCO Rulings
      • Other Recent Court Decisions and Developments
      • Conclusions
    • Final Section 263(a) Regulations Settled Many INDOPCO-Related Controversies
      • Amounts That Generally Must Be Capitalized
      • Acquired Intangibles for Which Capitalization Is Required
      • Created Intangibles for Which Capitalization Is Required
      • Other Intangibles Generally Must Be Separate and Distinct Assets for Capitalization to Be Required
      • Certain Transaction Costs Must Be Capitalized
      • Coordination of Section 263(a) Regulations with Rules for Accrual-Method Taxpayers
      • Separate Capitalization Rules for Amounts Paid to Facilitate Acquisitions, Restructurings, Contributions to Capital, Formations of Disregarded Entities, Etc.
      • Take Advantage of Taxpayer-Friendly Regulation Provisions
      • Tax Treatment of Capitalized Amounts
      • Impact of Section 263(a) Regulations on Pre-opening Expenditures Incurred to Internally Start Up a Brand New Business
      • Tax Compliance Drill for Pre-opening Expenditures Incurred to Internally Start Up a Brand New Business
      • Impact of Section 263(a) Regulations on Pre-opening Expenditures to Internally Expand an Existing Business
      • Impact of Section 263(a) Regulations on Pre-opening Expenditures Incurred in Connection with Same-Line-of-Business Acquisition
      • Tax Compliance Drill for Pre-opening Expenditures Incurred to Expand Existing Business (Internally or Via Acquisition)
      • Impact of Section 263(a) Regulations on Pre-opening Expenditures Incurred in Connection with Acquisition of Dissimilar Business
      • Tax Compliance Drill for Pre-opening Expenditures Incurred in Connection with Acquisition of Dissimilar Business
    • Real Estate Development and Capital Gains
      • Capital Gains from Selling Out
    • SE Tax on LLC Members
    • More on Unincorporated Businesses and the SE Tax
      • SE Tax Planning in Community Property States
      • Unincorporated Businesses in Non-community Property States
    • Update on Simplified Compliance Rules for Unincorporated Husband-Wife Businesses
      • How to Elect Out of Partnership Status
      • Definition of Qualified Joint Venture
      • IRS Admits Husband-Wife Rental Real Estate Business Can Be Qualified Joint Venture, but Watch Out for Tricky Tax-Reporting Procedure
      • Unofficial IRS Guidance Says Husband-Wife LLC Cannot Be Qualified Joint Venture
    • Using S Corporations to Reduce Social Security and Medicare Taxes
    • Evidence of IRS Interest in This Question
    • Conclusions
    • What about C Corporations?
    • Tax-Free Education Assistance for Owner's Employee-Child
      • Qualification Rules
      • Dodging the Ownership Rules
      • Effect on Financial Aid Eligibility
      • Additional Benefits from Other Education Breaks
    • Do Not Let the IRS Jam Accrual Accounting Change Down Clients' Throats
      • Recent (Mostly Favorable) Developments
      • Concrete Is Not "Merchandise"
      • Sand and Gravel Is "Merchandise" (Unless Tax Planning Saves the Day)
      • Two Exceptions Allow Cash Method for All Who Qualify
    • S Versus C Debate in Light of Reduced Individual Tax Rates
      • The Bottom Line
    • Business Tax Changes Included in the American Recovery and Reinvestment Act of 2009
      • Small and Mid-Sized Businesses Can Carry Back 2008 Losses Up to Five Years
      • Income Triggered by Reacquiring Taxpayer¡¯s Own Debt at Discount Can Be Deferred
      • Extension of $250,000 Section 179 First-Year Depreciation Allowance
      • Extension of 50% First-Year Bonus Depreciation Allowance
      • Extension of Corporate Option to Claim Certain Credits Instead of Bonus Depreciation Deductions
      • Break for Some 2009 and 2010 S Corporation Built-In Gains
      • Liberalized Gain Exclusion for New Issues of Small Business Stock
      • Liberalized Work Opportunity Tax Credit Rules
      • Elimination of Corporate ACE Adjustment for Interest on Tax-Exempt Bonds Issued in 2008 and 2009
      • Bigger Tax-Free Limit for Employer-Provided Transportation Fringe Benefits
      • Subsidized COBRA Coverage for Terminated Workers
      • Authorization of Additional New Markets Credits
      • Revocation of Problematic Section 382 Guidance for Banks
      • Liberalized Rules for High-Yield Debt Obligations
      • Controversial Withholding Rule for Payments to Government Contractors Postponed Until 2012
      • Another 2013 Estimated Tax Bump for Large Corporations
      • Expanded Alternative Motor Vehicle Credit Covers Plug-In Electric Vehicle Conversions (for Individuals and Businesses)
      • Overhauled Credit for Plug-In Electric Vehicles (for Individuals and Businesses)
      • New Credit for Low-Speed, 2-Wheeled, and 3-Wheeled Plug-In Electric Vehicles (for Individuals and Businesses)
      • Liberalized Credit for Alternative Fuel Vehicle Refueling Property (for Individuals and Businesses)
      • Expanded Business Alternative Energy Tax Breaks
    • Business Tax Changes in the Worker, Retiree, and Employer Recovery Act of 2008
      • Retirement Plans Must Give IRA Rollover Option to Non-Spouse Beneficiaries (Eventually)
      • Higher Failure-to-File Penalties for Partnerships and S Corps
      • Tons and Tons (and Tons) of Highly Technical Retirement Plan Changes
    • Business Tax Changes in the Emergency Economic Stabilization Act of 2008
      • Depreciation Extenders and Changes
      • Other Significant Business Extenders and Changes
      • Oil and Gas and Refining Industry Changes
      • Miscellaneous Business Extenders and Changes
      • Energy-Related Extenders and Changes
      • Disaster-Relief Business Tax Changes
      • Executive Compensation Tax Changes
    • Business Tax Changes in the Housing Assistance Tax Act of 2008
      • Starting in 2011: New Information Reporting Requirements for Credit Card, Debit Card, and Third-Party Network Sales
      • Corporations Can Use R&D and Minimum Tax Credit Carryovers Instead of Claiming Bonus Depreciation
      • Liberalized Rules for REITs
    • Business Tax Changes in the Food, Conservation, and Energy Act of 2008
      • New (but Delayed) Limit on Schedule F Farming Losses
      • Changes to Optional Self-Employment Tax Methods
      • Conservation Donation Breaks Extended for Two Years
      • Three-Year Depreciation for Racehorses
      • Conservation Reserve Payments to Retired and Disabled Individuals Exempted from SE Tax.. 1-112 Section 1031 Treatment for Swaps of Stock in Farm-Related Entities
      • New Farming Deduction for Endangered Species Recovery Expenses
      • One-Year Tax Cut for Timber Gains
      • Favorable REIT Tax Treatment for Timber Gains
      • Miscellaneous Changes
    • Business Tax Changes in the Heroes Earnings Assistance and Relief Tax Act of 2008
      • Enhanced Retirement Plan Benefits
      • New Rules for Differential Pay
      • New (but Temporary) Differential Pay Credit for Small Employers
      • Increased Minimum Failure-to-File Penalty
  • Chapter 2 - Implementing a Tax Planning System
    • Learning Objectives
    • Introduction
    • A Life Cycle Approach
      • Understanding the Problem
      • The Life Cycle Approach
      • Major Phases
    • Understanding the End Game
      • Maximizing After-Tax Cash Flow
      • Get It While You Can¡¦
      • Nonstatutory vs. Statutory Benefits
      • Schedule E Income
      • Salary Plans
      • Retirement Plans
      • Family Business Structure
      • Maximizing Equity Growth
      • Create Transferable Value (Goodwill)
    • Putting It All Together
    • Summary
  • Chapter 3 - Start-Up Issues
    • Learning Objective
    • Introduction
    • Directions
    • Part 1 - Case Study
      • Case 3-1 - Mom's Creamery
    • Part 2 - Toolkit Choice of Business Form
      • The Evolving Choice of Entity Landscape
      • Sole Proprietorships
      • Single-Member Limited Liability Companies
      • C Corporation Pros and Cons
      • Qualified Small Business Corporations (QSBCs)
      • S Corporation Pros and Cons
      • Multi-Member LLC Pros and Cons
      • Limited Liability Partnership (LLP) Pros and Cons
      • General Partnership Pros and Cons
      • Limited Partnership Pros and Cons
      • State Taxation
    • Formation Issues
      • §§351 and 357 for C and S Corporations
      • §1367 - S Shareholder Basis
      • Do Not Give Away the Intangibles
    • Hiring Family Members
      • By Sole Proprietors, Partnerships, and LLCs
      • By a Family-Owned Corporation
    • Including Debt in Corporate Capital Structures
      • Third-Party Debt
      • Owner Debt
      • How to Ensure That Owner Debt Will Be Respected As Such
    • Summary
    • Questions
  • Chapter 4 - Special Tax Considerations of Operations
    • Learning Objectives
    • Introduction
    • Quick Thoughts about Arranging for C Corporation Dividends, Stock Redemptions, and Stock Sales to Minimize Impact of Future Tax Rate Hikes
      • Strategy No. 1: Take Dividends Right Now
      • Strategy No. 2: Do Low-Taxed Stock Redemption Deal Right Now
      • Strategy No. 3: Sell Stock Right Now
      • The Bottom Line
    • Compensating C Corporation - Shareholder-Employees
      • What Is Reasonable?
      • Reasonable Compensation Checklist
      • Reasonable Compensation Court Decisions
      • Conclusions
    • Retirement Plan Options for Small Business Owners in a Nutshell
      • The Basics
      • Solo 401(k) Plan
      • Simplified Employee Pension (SEP)
      • Defined Contribution Keogh and Corporate Profit-Sharing Plans
      • SIMPLE-IRA
      • Defined Benefit Pension Plan
      • All about Solo 401(k) Plans
    • Benefits of Buy-Sell Agreements
      • What Is a Buy-Sell Agreement?
      • How Do They Work?
      • The Three Types of Buy-Sell Agreements
      • Funding Buy-Sell Agreement Purchase Obligations
      • Including Tax-Saving Terms in Buy-Sell Agreements
      • Estate Planning Benefits
      • Ensuring Buy-Sell Agreements Deliver the Expected Estate Planning Benefits
    • Converting a Corporation into an LLC (or LLP)
      • Watch Out for Goodwill and Other Intangibles
    • Depreciating Property Converted from Personal Use to Business Use (and Vice Versa)
      • Conversion from Personal Use to Business Use
      • Conversion from Business Use to Personal Use
      • When Change in Use Results in Different Recovery Period and/or Different Depreciation Method
      • Shorter Period and/or Faster Method after Change in Use
      • Longer Period and/or Slower Method after Change in Use
    • Heavy Tax Savings Still Available for "Heavy SUVs, Pickups, and Vans Used over 50% for Business
      • Maximum Deductions for Cars with Bonus Depreciation
      • Maximum Deductions for Cars without Bonus Depreciation
      • Maximum Deductions for Light Trucks and Light Vans with Bonus Depreciation
      • Maximum Deductions for Light Trucks and Light Vans without Bonus Depreciation
      • Clients Can Take Advantage of Better Depreciation Rules for "Heavy" Vehicles
      • Reduced $25,000 Section 179 Deduction for Heavy SUVs
      • Despite $25,000 Limitation, Depreciation Rules for Heavy SUVs Are Still 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
      • Other Section 179 Caveats
      • Clients Must Plan Ahead to Preserve Section 179 Tax Savings for Heavy Business Vehicles
    • Converting Unincorporated Small Businesses into S Corporations to Reduce Social Security and Medicare Taxes
      • How the SE Tax Works in a Nutshell
      • How S Corporation Status Could Reduce Social Security and Medicare Taxes
      • What If Client¡¯s Business Is Operated as a Partnership or Multi-Member LLC?
      • Conversion Mechanics for LLCs (Including SMLLCs)
      • Mind These Caveats
    • Summary
  • Chapter 5 - Business-Exit Considerations
    • Learning Objective
    • Introduction
    • Dispositions of the Business
      • Buyer Perspective
      • Seller Perspective
      • Flow-Through Advantage
      • Tax Impact of Corporate Liquidations
      • Tax-Wise Corporate Asset Sales
    • Sale of an Ownership Interest
      • Sale of Partnership Interest
      • Sale of S Corporation Stock
      • Best of Both Worlds - Stock Sale Treated as Asset Sale for Tax Purposes
      • Sale of C Corporation Stock
    • Selling Out to a Leveraged ESOP
    • Planning for Stock Redemptions by Family Corporations
    • Buying Out Spouse's Business Ownership Interest in Divorce
    • Divorce-Related Redemption of Corporate Stock
      • Scenario 1: Redemption Is Not Constructive Distribution to Non-Transferor Spouse
      • Scenario 2: Redemption Is Constructive Distribution to Non-Transferor Spouse
      • Election to Reverse the Tax Results
      • Election Timing Requirement and Effective Date Rules
    • Tax Planning Opportunities with Covenants Not to Compete
      • Tax Benefits of Minimizing Allocations to Covenants
      • Tax Benefits of Maximizing Allocations to Covenants
      • When Can a Covenant Be Supported?
    • Primer on Family Limited Partnerships (FLPs) and Family Limited Liability Companies (FLLCs)
      • What Are FLPs and FLLCs?
      • Estate and Gift Tax Issues
      • Avoid IRC Section 2036(a) Problems
      • Protect the Annual Gift Tax Exclusion
      • Federal Income Tax Issues
      • Impact of Recent Estate and Gift Tax Changes
      • Asset Protection Advantages
      • Practical Considerations
      • Conclusions on FLPs and FLLCs
    • Questions
  • Chapter 6 - Latest Developments

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Excerpts

Chapter 1 - Corporate Tax Trends

Learning Objectives

• Provide small business clients with up-to-date planning tips.
• Get up to speed on business tax changes included in recent legislation.

Introduction

Because this is an update chapter, it does not have a case study. Instead, it focuses on planning issues.

Taking Advantage of Planning Strategies Under the Current Tax Rate Structure (Before It Ends)

A few years ago, Congress significantly reduced individual federal income tax rates on ordinary income from salary, interest, alimony, and the like. As the law currently reads, these reduced individual rates will last through the end of 2010. Fingers crossed!

Even better, qualified dividends received through 2010 are taxed at a maximum individual rate of only 15%. Individuals whose dividends fall within the 10% and 15% ordinary income rate brackets will pay 0% for 2008-2010. These historically low rates apply equally to qualified dividends received by individual shareholders from their closely held corporations.

The same 15%/0% rates apply to most long-term capital gains from capital asset sales in 2008- 2010.

Sunset Rules. After 2010, dividends will again be taxed at ordinary income rates unless Congress takes further action and capital gains will be taxed at higher rates than under the current system. After 2010, ordinary income rates will return to 15%, 28%, 31%, 36%, and 39.6%.

The current 15%/0% rates apply only to qualified dividends paid on shares of corporate stock [IRC Sec. 1(h)(11)]. However lots of payments that are commonly called "dividends" are not qualified dividends under the tax law. For example,

• Dividends paid on credit union accounts are really interest payments. As such, they are considered ordinary income and are therefore taxed at regular rates – which can be as high as 35%.

• The same is true for dividends paid on some publicly traded preferred issues that are actually trust units wrapped around underlying bundles of corporate bonds. In other words, these issues are not really shares of stock in a corporation. Therefore, the dividends paid on these issues are taxed as interest at ordinary rates. Moral: clients should not buy preferred issues without knowing exactly what they are buying.

• Mutual fund dividend distributions that are paid out of the fund's short-term capital gains, interest income, and other types of ordinary income are taxed at regular rates. So, mutual funds that engage in rapid-fire trading will generate payouts that are taxed at ordinary income rates of up to 35% rather then at the optimal 15%/0% rates your clients might be hoping for.

• Bond fund dividends are also taxed at ordinary income rates, except to the extent the fund is able to reap long-term capital gains from selling appreciated assets.

• Here is some good news: mutual fund dividends paid out of (1) qualified dividends from the fund's corporate stock holdings and (2) long-term capital gains from selling appreciated securities positions are eligible for the 15%/0% rates. This means mutual funds' annual tax information statements must separately identify dividends eligible for the 15%/0% rates as well as ordinary income dividends that are taxed at regular rates.

• Most REIT dividends are not eligible for the 15%/0% rates. The main sources of cash for REIT payouts are usually not qualified dividends from corporate stock held by the REIT or long-term capital gains from asset sales. Instead most payouts are derived from positive cash flow generated by the REIT's real estate properties. So, most REIT dividends are taxed at ordinary income regular rates. Clients should not buy REIT shares with the expectation of benefiting from the 15%/0% rates.

• Dividends paid on stock in qualified foreign corporations are theoretically eligible for the 15%/0% rates. Here is the rub, these dividends are often subject to foreign tax withholding. Under the U.S. foreign tax credit rules, individual shareholders may not receive credit for the full amount of withheld foreign taxes. So they can wind up paying more than the advertised 15%/0% rates. [See IRC Secs. 1(h)(11)(C)(iv) and 904.]

Warning. To be eligible for the 15%/0% rates on qualified dividends, the stock on which the dividends are paid must be held for more than 60 days during the 120-day period that begins 60 days before the ex-dividend date (the day following the last day on which shares trade with the right to receive the upcoming dividend payment). Bottom line, when shares are owned only for a short time around the ex-dividend date, the dividend payout will be taxed at ordinary income rates [IRC Sec. 1(h)(11)(B)(iii)].

Congress has not changed the corporate federal income tax rate schedule. As has been the case for many years, a C corporation's income is taxed like this:

• 15% on the first $50,000 of income;

• 25% on income between $50,001 and $75,000;

• 34% on income between $75,001 and $100,000;

• 39% on income between $100,001 and $335,000;

• 34% on income between $335,001 and $10 million;

• 35% on income between $10,000,001 and $15 million;

• 38% on income between $15,000,001 and $18,333,333;

• 35% on income above $18,333,333.

Current Strategies for Closely Held C Corps

Taken together, the favorable federal income tax rate changes for individuals and the unchanged corporate rate schedule have important implications for clients who operate their businesses as C corporations. Here are five tax-saving strategies opened up by the currently low tax rates on qualified dividends.

Strategy 1: Pay Dividends Intentionally

Say your client is employed by his own C corporation. Avoiding the double taxation of corporate earnings has probably been this client's number one tax planning goal for years. Before the current era of low tax rates on dividends, the standard strategy was to "zero out" the corporation's taxable income each year (or nearly so) via compensation payments (salary and year-end bonus) to the shareholder-employee. As you know, legitimate payments for shareholder-employee compensation can be deducted by the corporation as ordinary and necessary business expenses [IRC Sec. 162(a)(1)].

Of course the shareholder-employee is then taxed on the compensation payments he receives. In addition, federal employment taxes must be paid (half by the corporation; the other half withheld from the shareholder-employee's salary and bonus checks). This is not a perfect situation, but it avoids double taxation.

Thanks to reduced tax rates on dividends, the cost of double taxation is now a lot less than before, because qualified dividends – including those from one's own closely held C corporation – are now taxed at no more than 15%. Still, double taxation is something that should always be avoided. Or is it?

What if the shareholder-employee's salary and bonus payments are fine-tuned to reduce the corporation's taxable income to $50,000 annually (or thereabouts)? Under the graduated federal income tax rate schedule for corporations, annual taxable income between zero and $50,000 is taxed at only 15%. So the tax bill on an even $50,000 of corporate taxable income is a mere $7,500 (15% × $50,000). Let us assume the corporation retains $50,000 of taxable income and pays the resulting tax bill.

Next, the corporation distributes $42,500 of after-tax cash to the shareholder-employee ($50,000 – $7,500). In most cases, that $42,500 will be a qualified dividend. So the shareholder-employee is taxed at only 15%, which means he owes $6,375 to the U.S. Treasury (15% × $42,500).

Under this intentional dividend strategy the shareholder-employee nets $36,125 after all federal taxes ($50,000 – $7,500 – $6,375).

What happens if the corporation instead follows the traditional strategy of zeroing out the last $50,000 of taxable income by paying the shareholder-employee a $50,000 year-end bonus? Assuming the shareholder-employee pays the maximum 35% federal rate, he owes $17,500 to the U.S. Treasury (35% × $50,000). Of course, he will also have federal employment taxes

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Videocourse Details

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