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Choice of Entity: An Overview of Tax and Non-Tax Considerations (Portfolio 1550)

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Choice of Entity: An Overview of Tax and Non-Tax Considerations discusses state and federal income tax and other considerations pertinent in choosing the most advantageous legal form for conducting business and investment activities. It provides a summary perspective on the various legal forms of business enterprises and their relative advantages and disadvantages. Written by Bruce P. Ely, Esq. and Christopher R. Grissom, Esq., both of the law firm Bradley Arant Rose & White LLP, this Portfolio examines both the tax and non-tax considerations of which a practitioner should be aware in advising a client on the choice of business form: sole proprietorship, general partnership, limited partnership, regular corporation, S corporation, LLC, LLP, LLLP, and business trust.  Selecting the form in which a business will operate is one of the most significant decisions a client starting a new business, or continuing an existing one, will have to make.  

This Portfolio also provides practitioners with a checklist to which they may refer in advising clients on the choice of entity, i.e., to assist practitioners in making certain they have considered all the issues that could materially affect a recommendation to a client on this complicated issue, including: 

  • “Check-the-box” regulations, limited liability, administrative requirements (required documents, tax returns, etc.), reasonable compensation, retirement plans, and employee fringe benefits,
  • Tax-planning opportunities pertinent to choice-of-entity regarding income tax planning and estate planning, and
  • Requirements and procedures for changing the form of the business. 

In addition, Choice of Entity: An Overview of Tax and Non-Tax Considerations provides an analysis of the relevant principles of federal and state law that govern choice-of-entity decisions. Because this Portfolio is a survey, however, touching upon a broad range of topics that could affect a choice-of-entity decision, the authors have, in many cases, summarized principles of law.  Discussions of state law are generally limited to individual state examples or references to uniform state acts such as the Model Business Corporation Act, the Revised Uniform Partnership Act, and the Revised Uniform Limited Partnership Act. Discussions of complex areas of federal law, such as federal income taxation of deferred compensation plans and the minimum and alternative minimum tax, examine the essential principles of law involved, with emphasis on how they affect choice-of-entity decisions.

Choice of Entity: An Overview of Tax and Non-Tax Considerations allows you to benefit from: 

  • Hundreds of hours of original research on specific tax planning topics from leading practitioners in this area.
  • Invaluable practice documents including tables, charts and lists.
  • Plain-English guidance from world-class experts.
  • Real-world and in-depth analysis that lets you explore various options.
  • Time-saving access to relevant sections of tax laws, regulations, court cases, IRS documents and more.
  • Alternative approaches to both common and unique tax scenarios. 

This Portfolio is part of the Premier State Tax Library , a comprehensive series, which covers major state tax transactions and issues with expert, in-depth analysis, and offers commentary on a wide range of multi-state and state-specific taxation topics, including Sales and Use, Corporate Income, Individual Income, Property, Gross Receipts, Limitations on States' Authorities to Tax, Credits and Incentives, Electronic Commerce, Mergers and Acquisitions, Procedure and Administration, Special Industries, and more.

Detailed Analysis

1550.01. INTRODUCTION

1550.02. CHOOSING THE BUSINESS ENTITY: THE VARIOUS FORMS IN WHICH BUSINESS CAN BE CONDUCTED

A. Introduction

B. The Sole Proprietorship

1. In General

2. Organization of a Sole Proprietorship

3. Operation of a Sole Proprietorship

4. Transfer of Interest in a Sole Proprietorship

5. Termination of a Sole Proprietorship

6. Assessment of the Sole Proprietorship as a Form of Doing Business

C. The General Partnership

1. In General

2. Organization of a Partnership

3. Operation of a Partnership

4. Transfer of Interest in a Partnership

5. Termination of a Partnership

6. Assessment of the Partnership as a Form of Doing Business

7. LLP

D. The Limited Partnership

1. In General

2. The Publicly-Traded Limited Partnership

E. The LLLP

F. The C Corporation

1. In General

2. Organization of a Corporation

3. Operation of a Corporation

4. Transfer of Interest in a Corporation

5. Termination of a Corporation

6. Assessment of the Corporation as a Form of Doing Business

G. The S Corporation

1. In General

2. Organization and Eligibility for S Corporation Status

3. Operation of an S Corporation

4. Transfer of Interest in an S Corporation

5. Termination of an S Corporation

6. Subsidiaries

7. Assessment of the S Corporation as a Form of Doing Business

H. The LLC

1. In General

2. Organization of an LLC

3. Operation of an LLC

4. Transfer of Interest in an LLC

5. Termination of an LLC

6. Single Member LLCs

7. Assessment of the LLC as a Form of Doing Business

8. "Series" LLCs

I. The Professional Corporation or Association; the Partnership Including PCs or Associations

1. In General

2. Organization of a PC

3. Operation of a PC

a. Formalities

b. Income Taxation of PIPiCs: I.R.C. § 269A

4. Transfer of Interest in a PC

5. Termination of a PC

6. Assessment of the PC and PIPiC as a Form of Doing Business

J. Other Forms of Business Organization

1. The Joint Stock Company

2. The Business Trust

3. The Delaware Headquarters Management Corporation

1550.03. VARIOUS TAX AND NON-TAX CONSIDERATIONS IN CHOOSING THE APPROPRIATE BUSINESS FORM

A. The Check-the-Box Regulations

1. The 1996 Final Regulations

2. Classification as a "Business Entity"

a. Corporations

b. Partnership

c. Limited Liability Companies

d. Trusts

e. Domestic Eligible Entities

f. Foreign Eligible Entities

g. Entities in Existence Prior to January 1, 1997

3. Making an Election

B. Limited Liability

1. In General

2. The Sole Proprietorship

3. The C Corporation

4. The S Corporation

5. The Partnership

6. The Limited Partnership

7. The Limited Liability Company

C. Administrative Requirements: Required Documents, Tax Returns, Etc.

1. In General

2. The Sole Proprietorship

a. Non-Tax Considerations

b. Tax Considerations

3. The Partnership

a. Non-Tax Considerations

b. Tax Considerations

(1) Tax Returns

(2) Partnership Taxable Year

4. The Limited Partnership

a. Non-Tax Considerations

(1) Documents to File

(2) Limited Partners' Rights

b. Tax Considerations

5. The C Corporation

a. In General

b. Non-Tax Considerations

(1) Articles of Incorporation

(2) Bylaws

(3) Board of Directors

(4) Shareholders

(5) Other Non-Tax Administrative Requirements of Corporations

c. Tax-Related Administrative Requirements of C Corporations

6. S Corporations

a. Non-Tax Considerations

b. Tax Considerations

(1) Tax Returns

(2) S Corporation Taxable Year

7. Limited Liability Company

a. Non-Tax Considerations

b. Tax Considerations

D. Reasonable Compensation

1. C Corporations

2. S Corporations

E. Retirement Plans and Employee Fringe Benefits

1. Tax-Qualified Retirement Plans

2. Employee Fringe Benefits

F. Employment Taxes

G. Treatment of Capital Gains and Losses

H. Accumulated Earnings Tax and Personal Holding Company Tax

I. Alternative Minimum Tax (AMT)

1. Introduction

2. Computation

a. In General

b. Differences Between C Corporations and Other Taxpayers

(1) Tax Rate

(2) Exemption Amount

(3) Adjustments

(4) Other

(5) State AMT

3. Effect of Recordkeeping Burden

J. Reduction of C Corporation Preference Items

K. Problems Involving Reallocation of Income

1. In General

2. Assignment-of-Income Doctrine

3. Section 482

4. Section 269

5. Section 269A

L. Limitations on Passive Losses and Credits

M. Other Considerations

1. Deductibility of Net Operating Losses

2. Deductibility of Charitable Contributions

3. Treatment of Tax-Exempt Income

4. Securities Law Considerations

5. Accounting Methods Available

a. In General

(1) Cash Method

(2) Accrual Method

(3) Other Permissible Methods

(4) Hybrid Methods

b. Sole Proprietorship

c. Partnership

d. C Corporation

e. S Corporation

f. Limited Liability Company

g. Comparisons

6. 1993 RRA Small Business Provisions

1550.04. TAX-PLANNING OPPORTUNITIES PERTINENT TO CHOICE OF ENTITY

Introductory Material

A. Income Tax Planning

1. Income-Splitting Between the Business Entity and Its Owners

a. Benefits of Income-Splitting

b. Means of Achieving Income Splitting

(1) Payment of Compensation to Employee-Owner

(2) Renting to the Corporation

(3) Other Methods

c. Possible IRS Attacks on Income-Splitting Between a C Corporation and Its Owners

(1) Accumulated Earnings Tax

(2) Personal Holding Company Tax

(3) Constructive Dividends

(4) Assignment of Income and Related Doctrines

2. Income–Splitting Between Business Owners and Family Members

a. Employing Family Members in the Business

b. Leasing From Family Members

c. Family Members as Principals: Family Partnerships and Family Members as Shareholders of S Corporations or C Corporations

(1) The C Corporation

(2) Family Partnerships (or Family LLCs)

(3) S Corporations with Family Members as Shareholders

3. Pass-Through and Special Allocation of Tax Items

4. Dividends and Other Investment Income

5. Loss Deduction on Worthlessness of Business

B. Estate Planning

1. Special Considerations in Estate Planning for a Business Owner

a. Liquidity Problems

b. Risk of Protracted Disputes

c. Tension Between Participating and Non–Participating Offspring

d. Balancing Interests of Unrelated Persons

2. Estate Planning and the Sole Proprietorship

3. Sale, Redemption, or Liquidation of Interest at Death

a. Sale or Redemption of Stock Versus Sale of Partnership or LLC Interest

b. Sale or Redemption of Stock Versus Liquidation of Partnership or LLC Interest

c. Effect of Insurance or Accumulation of Earnings for Funding the Purchase of a Decedent's Interest

d. Effect of Purchase or Liquidation of a Decedent's Interest in a Family-Held Business

4. Conclusions

1550.05. CHANGING THE FORM OF THE BUSINESS

Introductory Material

A. Changing the Form of a Sole Proprietorship

1. Control Requirements

2. Gain Recognition

3. Sales and Use Taxes

B. Incorporating a Going Business

1. Introduction

2. Transfer of Ordinary Income Assets and Current Liabilities

3. Carryover of Tax Attributes

4. The Problem of the Service Provider

5. Incorporating a Partnership

6. Taxable Incorporations

C. Changing from an S Corporation to a C Corporation

D. Changing from a C Corporation to an S Corporation

E. Changing from Corporate to Non-Corporate Status

F. Converting an Existing Business to an LLC

Working Papers

Item Description Sheet

Worksheet 1 Checklist of Significant Information to Obtain from Client with Respect to Choice of Entity

Worksheet 2 Checklist of Analytical Steps in Making the Choice-of-Entity Decision

Worksheet 3 Checklist of Significant Non-Tax Factors Pertinent to Choice of Entity

Worksheet 4 Checklist of Significant Tax Factors Pertinent to Choice of Entity

Worksheet 5 Checklist of Significant Differences Among S Corporations, Partnerships, Limited Liability Companies, and Limited Partnerships

Worksheet 6 Sample Letter to Client on Choice of Entity

Worksheet 7 IRS DOCUMENTS

Worksheet 8 State Tax Treatment of Limited Liability Companies and Limited Liability Partnerships

Worksheet 9 Limited Liability Partnerships State-by-State Summary

Worksheet 10 Tabular Analysis - Choice of Business Entity Issues

Worksheet 11 TAX TREATMENT OF LLCs/LLPs/LPs ("LLEs") BY STATES IMPOSING NET WORTH- OR DEBT-BASED CORPORATE FRANCHISE TAXES

Worksheet 12 State Tax Treatment of LLCs and LLPs- Nonresident Member/Partner Withholding

Worksheet 13 State Nonresident Withholding and Composite Return Requirements for Pass-Through Entities

Worksheet 14 Limited Liability Companies and Cross Entity Mergers

Worksheet 15 Limited Liability and Conversion Statutes

Worksheet 16 A Comparison of Business Laws and Taxation (Part I)

Worksheet 17 A Comparison of Business Laws and Taxation (Part II)

Worksheet 18 Finding Neverland: Will Delaware's New Corporate Entity Help Taxpayers Escape the Hooks of State Anti-PIC Laws?

Bibliography

BIBLIOGRAPHY

Bruce Ely
Bruce P. Ely, B.S., cum laude, in 1977 from the University of Alabama and his J.D. degree in 1980 from the University of Alabama School of Law. In 1981, he received his LL.M. in Taxation from New York University School of Law; past Chairman of the Tax Section of the Alabama State Bar and serves as state and local tax adviser to the 5,000 member Business Council of Alabama; state tax editor for the Business Entities Journal and a contributing editor to State Tax Notes, State Income Tax Alert, and BNA Multistate Tax Report; Fellow of the American College of Tax Counsel, member of the BNA Multistate Tax Advisory Board, Trustee of the American Institute on Federal Taxation; active member of both the Partnerships Committee and State and Local Tax Committee of the ABA's Section of Taxation.  Mr. Ely was a principal author of the Alabama S Corp. Act, the Alabama LLC Act, and the Alabama LLP Act, and co-authored the ABA's Model State S Corp. Income Tax Act and The Alabama LLC Handbook; lecturer at the law schools of New York University, Georgetown University, and Vanderbilt University, and has served as an adjunct professor at the University of Alabama School of Law.
Christopher Grissom
Christopher R. Grissom is a senior associate in the Birmingham, Alabama office of Bradley Arant Rose & White LLP. His practice involves state and local tax planning, LLCs, and federal and state tax disputes. Mr. Grissom received his B.S. in 1993 from the University of Alabama's Culverhouse School of Accountancy and his law degree, cum laude, in 1997 from the University of Alabama School of Law, where he was a student editor of The American Journal of Tax Policy. He is a contributing editor to State Tax Notes, State Income Tax Alert, Journal of Multistate Taxation, and BNA Multistate Tax Report. In addition, he is a member of the ABA Section of Taxation and the Alabama State Bar Section of Taxation.