Larry's Tax Law

For so many of us, 2023 has been a difficult year.  The so-called end of the COVID-19 pandemic looked to be a bright spot in our lives, but with wars raging in Ukraine and Gaza and dramatic social unrest at our doors, we continue to face difficult times.

I am extremely grateful for the unwavering support of family, friends, clients, and my law colleagues, especially in these troubling times!

During these trying times, we have had to be mindful of the good that surrounds us.  As the Ancient Greek philosopher Aristotle is accredited with saying:

“It is during our darkest moments that we must focus to see the light.”

During 2023, I was able to speak in person at several tax conferences.  It was wonderful to actually see and visit with conference attendees rather than delivering a lecture into a computer screen’s virtual abyss.  This year, I was fortunate to have the opportunity to speak at the following tax conferences:

The 82nd Institute on Federal Taxation (IFT) will be held in New York City on October 22-27, 2023, and in Berkeley, California, on November 12-17, 2023.

This year, I will be presenting my latest white paper, “A Journey Through Subchapter S / A Review of the Not So Obvious & The Many Traps That Exist for the Unwary.”  Our discussion will examine the potpourri of issues arising from Subchapter S that may not be readily apparent to the tax practitioner, such as matters arising from the single class of stock requirement, the built-in-gains tax, the interplay between Subchapter C and Subchapter S, lingering E&P, and late (or never made) elections.  The session will also alert tax practitioners to traps that exist for the unwary and, in some cases, possible ways to avoid or remedy falling into one of these traps.

I am pleased to announce that I will be presenting at the 49^th Annual Notre Dame Tax & Estate Planning Institute in South Bend, Indiana.  The Institute this year will occur on September 20-22. 

I will be presenting my white paper "Entity Classification – The Check-The-Box Regulations Revisited."  My discussion will cover recent developments in the law relating to entity classification, limitations under the check-the-box regulations, flexibility and planning opportunities created by the regulations, traps that exist for the unwary, and practical planning strategies for tax advisers.

I am extremely grateful to have the opportunity to speak at the Notre Dame Tax & Estate Planning Institute and present among a tremendous panel of speakers, including Jerry Hesch, Paul Lee, Jonathan Blattmachr and Stephen Breitstone.  It looks to be a terrific program for income tax and estate tax attorneys.

View the complete agenda and register using the link to attend the institute in person or to obtain the audio recording and the materials.

As you may be aware, the Corporate Transparency Act (the “CTA”) is a new federal law that requires most U.S.-based companies, including corporations, partnerships and limited liability companies, to report information regarding their “beneficial owners” to the federal government through the Financial Crimes Enforcement Network (“FinCEN”) and a new FinCEN IT system known as the Beneficial Ownership Secure System (“BOSS”).  The intent of the CTA and the reporting to FinCEN is to combat money laundering, tax fraud and other illegal activities.

The CTA reporting requirements will become effective on January 1, 2024, for newly formed companies (which do not otherwise qualify as exempt); provided, however, existing non-exempt companies have until January 1, 2025 to comply.

On April 5, 2023, Commissioner Daniel I. Werfel issued the Internal Revenue Service Inflation Reduction Act Strategic Operating Plan (“Plan”).  The Plan, which spans over 145 pages, is a roadmap to how the Service will deploy over the next decade the approximately $80 billion in supplemental funding it will receive as a result of the Inflation Reduction Act enacted by Congress last year (“IRA”).

In the Plan, Commissioner Werfel sums up the strategic goals for the IRS as follows:

“We will make it easier for taxpayers to meet their tax responsibilities and receive tax incentives for which they are eligible. We will adopt a customer-centric approach that dedicates more resources to helping taxpayers get it right the first time, while addressing issues in the simplest ways appropriate. We will address noncompliance, using data and analytics to expand enforcement in certain segments. We will become an employer of choice across government and industry. These changes will enable us to serve all taxpayers more equitably and in the ways they want to be served.”

It is a rainy day in the Pacific Northwest with chances of snow showers.  For those taxpayers that reside in the state of Washington or own highly appreciated capital assets located in the state, their day just got a bit gloomier. 

Earlier today, the Washington Supreme Court, in a 7-2 opinion, overturned the Douglas County Superior Court decision that had ruled the state capital gains tax enacted by the legislature in 2021 violates the Washington State Constitution.  

Majority Opinion

In its 50-plus page opinion written by Justice Debra L. Stevens, the majority of the court concludes:

“The court below [the Douglas County Superior Court] concluded the tax is a property tax that violates article VII’s uniformity requirement. In light of this ruling, the court did not address Plaintiffs’ additional constitutional challenges. We accepted direct review and now reverse. The capital gains tax is appropriately characterized as an excise because it is levied on the sale or exchange of capital assets, not on capital assets or gains themselves. This understanding of the tax is consistent with a long line of precedent recognizing excise taxes as those levied on the exercise of rights associated with property ownership, such as the power to sell or exchange property, in contrast to property taxes levied on property itself. Because the capital gains tax is an excise tax under Washington law, it is not subject to the uniformity and levy requirements of article VII. We further hold the capital gains tax is consistent with our state constitution’s privileges and immunities clause and the federal dormant commerce clause. We therefore reject Plaintiffs’ facial challenge to the capital gains tax and remand to the trial court for further proceedings consistent with this opinion.”

INTRODUCTION

As I have discussed in prior blog posts (March 11, 2013, April 9, 2013 and December 9, 2013), worker classification has historically been a focus of attention of various government agencies as well as others.  Misclassifying workers, even if unintentional, can create nightmares for businesses and their owners. 

The worker classification rules are not always objective, making them difficult to apply.  Additionally, the rules applicable to a particular business may vary depending on who is looking at the matter.  For example, in many cases, the laws applied by the Department of Labor (“DOL”) and the Internal Revenue Service (“IRS”) differ from the laws applied by state or local agencies.  On top of that, the laws of the states are not uniform.

As a result of the COVID-19 pandemic, we have seen a significant worldwide change in the structure of workforces caused by the emergence of the remote worker.  The number of remote workers has significantly multiplied in the last two years, adding one more factor to the worker classification analysis.  In and of itself, having workers performing services from remote locations (usually their personal residences) does not make the workers per se employees or per se independent contractors.  While the location where a worker performs services should be considered in making a classification determination (i.e., whether the business can or does control the worker), it is not a definitive factor.  Nevertheless, with a changed workforce model, which is likely here to stay, businesses should invest the time and energy in revisiting their prior worker classification conclusions to see if they remain valid today.    

2022, like the prior two years, has been difficult.  The COVID-19 pandemic and social unrest continues to be at the forefront of our existence.  On top of that, inflation and possible recessionary times are among us.

Thanks to the unwavering support of family, friends, clients, and colleagues, we are enduring through these turbulent times.  I am so grateful for these relationships!

I have had to constantly be mindful of the good things going on around us.  As American Poet Walt Whitman is accredited with saying:

By motion dated November 3, 2022, the Washington State Attorney General asked the Supreme Court of the State of Washington to allow the Washington Department of Revenue to implement and collect the capital gains tax struck down as unconstitutional by the Douglas County Superior Court, pending the high court’s ultimate ruling on the matter. 

As previously reported, the tax, which was set to go into effect on January 1, 2022 was struck down by the Douglas County Superior Court as unconstitutional.  The first tax payments under the new tax regime would be due on April 17, 2023.

Introduction

More than two decades ago, the Service announced its intention to consider simplifying the entity classification rules in Notice 95-14.  It stated:

“The Internal Revenue Service and the Treasury Department are considering simplifying the classification regulations to allow taxpayers to treat domestic unincorporated business organizations as partnerships or as associations on an elective basis. The Service and Treasury also are considering adopting similar rules for foreign business organizations. Comments are requested regarding this and other possible approaches to simplifying the regulations.”

The Service asked for public comments on simplification of entity tax classification.  It scheduled a public hearing on the matter for July 20, 1995. 

In May 1996, proposed entity classification regulations were issued by Treasury.  About seven months later, on December 17, 1996, Treasury finalized the regulations.  The regulations are found in Treasury Regulation Section 301.7701.

The regulations were clearly designed to accomplish the IRS’s stated goal – simplifying entity tax classification.  The regulations, commonly referred to as the “Check-the-Box” regulations, successfully brought an end to much of the long existing battle between taxpayers and the Service over entity tax classification.  The regulations generally became effective on January 1, 1997.  In a little over a month from now, they will be 25-years old.  

The regulations, despite judicial challenge (e.g., Littriello v. United States, 2005-USTC ¶50,385 (WD Ky. 2005), aff’d, 484 F3d 372 (6^th Cir. 2007), cert. denied, 128 S. Ct. 1290 2008)), have persevered, making the entity classification landscape free of many tax authority challenges and providing taxpayers with some objectivity and more importantly, much needed certainty.  That said, despite the simplification brought into the world of entity tax classification by the Check-the-Box regulations, for which tax practitioners applauded the government, several new hazards were created.  Whether these new hazards were intentional or unintentional is subject to debate.  Unfortunately, not all of these hazards are obvious to taxpayers and their advisors.  If taxpayers and their advisors are not extremely careful in this area, disastrous unintended tax consequences may exist.  Accordingly, a good understanding of the regulations and the consequences of making, not making or changing an entity tax classification decision is paramount.

Last month, I presented a White Paper that I authored on the regulations at the NYU 81^st Institute on Federal Taxation in New York City, and I will be presenting it again for NYU in San Diego on November 17, 2022.  The paper provides exhaustive coverage of the regulations and covers numerous nuances and traps that exist for unwary taxpayers and their advisors.  An issue which is often overlooked by practitioners is whether using the regulations to change entity status for income tax purposes is always a good idea.  While I discuss the issue in some detail in the paper, the sub-issue of whether a taxpayer should use the regulations to change the tax status of a limited liability company (“LLC”) taxed as a partnership to a corporation taxed under Subchapter S needs discussion.  I explore that sub-issue below.