Lewis C. Taishoff, Author at Think Outside the Tax Box

AUTHOR SPOTLIGHT

Lewis C. Taishoff

An author, teacher, advocate and trusted advisor, Lew Taishoff is a New York City-based attorney with 55 years of experience in corporate and individual tax and real estate matters. He is admitted to practice before the United States Tax Court. He was formerly, for ten years, an Enrolled Agent, examined and admitted to practice before the Internal Revenue Service. Lew Taishoff provides a high level of legal service to clients in the areas of tax and real estate. Individuals and businesses looking to buy, sell or lease property in the City as well as those trying to navigate the ever-evolving and complex tax landscape find experience, knowledge and dedication from Lew Taishoff.

You can learn more about Lew Taishoff at his website - https://taishofflaw.com/.

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Tax Court Roundup June 2023

This month I’ve decided to change format. I’m grouping Tax Court thumbnails by category. Not every reader deals with every issue. But coverage is still useful even where only a few specialize. Click here to read the latest happenings!

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TAX COURT ROUNDUP – February 2023

January brought some new wrinkles. Even tax practitioners whose endeavors are far from Tax Court can find useful information there. My usual reminder: I cover Tax Court exclusively. Tax Court decisions get appealed routinely, and reversed sometimes, so check before citing as authority…

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TAX COURT ROUNDUP – October 2024

Much of what happens in Tax Court is run-of-the-mill. Once the tax general practitioner learns the jurisdictional limits and procedural moguls, s/he can advise clients whether to spend the sixty bucks and the certified mail fees when TAS, Examination or Appeals can’t deliver an acceptable result. Following the Court’s orders and opinions for a while should do that. I try to present the less-than-usual, below-radar points for generalists and specialists.

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TAX COURT ROUNDUP – NOVEMBER 2023

A very mixed bag this month: IRS shifting ground on the eve of trial, plenty of discovery, loyalty programs, the end of the road for meaningful Section 6751(b) supervisory approval, and arrival of a new Special Trial Judge. And, as always, a lot of questions.

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TAX COURT ROUNDUP – May 2025

Once again, Tax Court provides slices of life as well as hyper-technical drilldowns into convoluted legal conundrums. To any who say that tax law is dull, I refer them to the annals of 400 Second Street, NW, where anything goes.

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TAX COURT ROUNDUP – MARCH 2024

February was Discovery Month at Tax Court. The high-deficiency, high-profile conservation easement cases coming from IRS crackdown put a premium on the old continuing legal education staple “win your case at discovery.” But it doesn’t go so well for shotgun demands, nor for broad-spectrum claims of privilege. Of course, more was resolved than just discovery disputes, but I’ll get to those.

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TAX COURT ROUNDUP – June 2024

No dramatic developments this month, but some technical inputs worth noting. A good practitioner is always learning; it’s so much better to learn from other peoples’ mistakes than one’s own.

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TAX COURT ROUNDUP – July 2024

Month’s-end brought signs of things to come. Earlier we saw clarification of the non-jurisdictional limit in employee classification cases, a new IRS tactic in syndication conservation easements, and, as always, sharpeners for the practitioner’s toolkit.

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TAX COURT ROUNDUP – January 2025

No holiday break for US Tax Court, as fresh developments arise, and some old doctrines need reenforcing. As usual, we’ve got both common problems and arcana on the radar, with one potential blockbuster.

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TAX COURT ROUNDUP – JANUARY 2024

The last month of 2023 featured more technical expositions than policy discussion. Practitioners will find insights worth their time. Generalists shouldn’t overlook some nuggets here. As always, Tax Court sees and deals with more varieties of income taxation than any other court.

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TAX COURT ROUNDUP – February 2025

When we enter upon a new Administration, we wonder at the shape of things to come. But surely since 1916, we have never had an incoming Administration promise us a repeal of the income tax and the reestablishment of the import tariff as the principal source of Federal funding. I would not, however, immediately cease to follow the proceedings of the US Tax Court.

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TAX COURT ROUNDUP – FEBRUARY 2024

New year, new rules, the changing features of United States Tax Court practice and procedure confront the tax practitioner (even those who don’t practice in Tax Court themselves), who must keep current among all the demands on our time, especially as the season opens. Let’s jump in.

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TAX COURT ROUNDUP – DECEMBER 2023

Despite the five days off for the two Federal holidays this month, there’s plenty from Tax Court, for both specialists and general practitioners. No other Court gets as deep into the “wrinkled skin” of US tax law. As always, there’s something for (almost) everyone.

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TAX COURT ROUNDUP – August 2024

What seemed to be a slow month turned out to have some intriguing developments, a new online petition generator for self-representeds, and new Judges joining the Tax Court bench (at long last).

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Tax Court Roundup – August 2023

The dog days, the doldrums, the get-out-of-town days…they’re here. The United States Tax Court is not immune, as the blockbuster cases and newsletter headliners have largely vanished. Still, there are report-worthy stories, despite the call of seashore and mountain meadow.

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TAX COURT ROUNDUP – APRIL 2024

Tax Court concludes tax season this year with a webinar on Practical Perspectives on Discovery, chaired by Judge Greaves, on April 16, 11:00 a.m. Eastern. With all the discovery jousting accompanying conservation easements and other high-dollar litigation, this is a must for all practitioners, so I’m headlining it. Information and registration on the Tax Court website.

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TAX COURT ROUND-UP – January 2023

I’m new here, but I know enough not to try to do what everyone else does. I won’t try to cover the wider tax picture. I cover United States Tax Court on my blog, so here’s a brief round-up on what went on in Tax Court during the last month that I think is of interest to the tax planner and practitioner…

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CURRENT EDITION

Summertime Marketing in Your Tax & Accounting Firm

Tax season is prosperous, summer is dry until extension season. Do you find yourself in that cycle? Clients are “easy” to get during tax season when taxes are top of mind. Then the direct deposits go dry by June, and you are looking for what’s next. Stop the search, you don’t have to add another service. You need better marketing to highlight the service that you offer and specialize in. This will allow you to have a predictable client pipeline. You can do tax preparation, planning, and or representation all year long.

Observations on the House-Passed OBBB

This article focuses on the OBBB from the House offering a variety of observations to help understand the range of changes, relevance to compliance and planning, process considerations and some unexpected provisions. While the final OBBB will not include all of the House provisions or will modify some of them, there are lessons to learn to understand the tax legislation process and results now and in the future.

Client Retention as a Prospecting Strategy: Turning Current Clients into Referral Sources

In the competitive accounting world, where trust and reliability are paramount, client retention is not just a success metric—it’s a vital strategy for sustainable growth. For Certified Public Accountants (CPAs), accountants, and bookkeepers, maintaining a solid relationship with existing clients can unlock new business opportunities, turning satisfied clients into powerful referral sources.

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  • How to Pay Less Tax on S Corporation Distributions

    Most taxpayers understand that having an S corporation often eliminates the so-called “double tax” issue C corporations pose. However, the majority of S corporations begin as C corporations and the activity that occurred during the time it was a C corporation will determine how and when to tax distributions from the S corporation. C corporations cannot avoid double taxation on profits simply by electing to be treated as an S corporation (yet there are many other ways to save this double tax on C corporations, stay subscribed to learn about them). Withdrawing C corporation profits even when it later becomes an S corporation can create an extra tax. Here’s how to avoid that.

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    COVID Tax Relief Allows Companies to Make Tax-Free COVID-19 Payments to Employees

    For a business owner, almost nothing in life is more uncertain than running a company during a pandemic. Like most people, worry about your own livelihood, family, friends, and loved ones and how you’ll cope during COVID-19 is at the top of your mind. But unlike others, you’ve got the added concern about your employees – both for their health and safety, as well as their financial health. While the government made some relief available in the earlier days of the pandemic such as forgivable loans like the Paycheck Protection Program (PPP) and Emergency Injury Disaster Loans (EIDL) one of the biggest benefits provided has to do with a little known tax provision to the tax law. This provision makes it possible to provide certain payments without tax during a terrorist attack or disaster, but if it weren’t for a certain interpretation of President Trump’s declaration in March 2020, this benefit wouldn’t exist for COVID-19.

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    Can I “Nominee” Income From a Schedule C to Another Return?

    I have a few physician clients who earn their income via Form 1099 and are perfect candidates for an S corporation. However, the hospital won’t issue the Form 1099 in the name/EIN of an S corporation. Is this an issue? Can I still report the income on the Form 1120S and report the Form 1099 on a Schedule C with a negative adjustment for the same amount and attach an explanation annually? Or is there any other way?

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    Year-End Tax Strategies for the Investor

    The end of the year is a time for holidays, family, and maybe overindulging at the dinner table. It can also be a time for substantial tax savings. There are many techniques a taxpayer can use to minimize their tax burden for the year. The key to many of them is acting before the calendar year comes to a close. Specifically, let’s examine tax strategies for the taxpayer with investments, such as stocks, bonds, and mutual funds. These strategies can help taxpayers lower taxes, keep more money in their pockets, and donate to their favorite charities.

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    More Cash Available for Employers Under Refundable Tax Credit

    As 2020 winds to a close, we have seen many beneficial programs provided by the Coronavirus Aid, Relief, and Economic Security Act (CARES Act) and the Families First Coronavirus Response Act (FFCRA). While most media coverage has focused on loans to employers such as PPP and EIDL, it is important to remember some of the lesser covered programs also included in the tax relief programs. In fact, eligible businesses may qualify to get cash back in some instances. The employee retention credit (ERC) under the CARES Act offers a refundable payroll tax credit for certain wages and health plan expenses paid by businesses during the economic hardship. However, many business owners have uncertainty as to how to qualify when they have also received a PPP loan. The paid sick leave and paid family medical leave credits also offer a refundable tax credit for qualifying wages and Medicare tax and health plan expenses. These refundable tax credits are stackable for maximum benefit when used correctly. Read on to discover how to qualify.

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    PPP Loan Forgiveness: Now What?

    It’s finally here! After much political wrangling, Congress and President Trump signed the Consolidated Appropriations Act, 2021 (HR 133) into law on December 27, 2020. Attached to this omnibus spending bill were a number of unrelated pieces of legislation, including the latest COVID-19 relief and stimulus measures. The law puts much needed cash in the hands of business owners and individuals alike, while Congress thumbs its collective nose at the IRS by including an override of the recent notice disallowing the deduction of expenses paid for using PPP funds. Several more key provisions in the new legislation’s Division N include process simplification and forgiveness for PPP borrowers, which will make life easier for everybody. To find out how to qualify for new rounds of stimulus, automatic forgiveness, and how to get both tax credits and free money, keep reading.

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    Why Can’t I Deduct PPP Payroll Expenses?

    Question: Given the recent passing of the stimulus law (CAA 2021) permitting a business to deduct payroll expenses paid with Paycheck Protection Program (PPP) funds, how does an S corporation or Partnership basis negatively impact this? I’m hearing that even though the law allows the deduction, some businesses will have suspended losses due to PPP funds. Which is true? Can a business deduct losses from PPP payroll or not?

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    Bob Dylan Shows How to Beat an Imminent Tax Increase

    Timing might be one of the oldest, most valuable tax strategies known. Essentially, a timing strategy allows a taxpayer to pay tax when rates are generally lower rather than when in a higher tax bracket or when facing increasing tax rates. Given this, 2020 may have been an optimal time to sell capital assets if tax rates rise under the new administration. President-elect Joe Biden has suggested taxing capital gains as ordinary income for high-income taxpayers (more than $400,000), as well as raising the top tax rate from 37% to 39.6%. Here’s how to cash in on the lower rates and, more importantly, when. While tax law changes seldom pass quickly, we often see changes made retroactive to the beginning of the year they are voted into law. Based on a recent story in The New York Times, Bob Dylan may have anticipated the increase when he sold the copyrights to his catalog of more than 600 songs for $300 million. Not to fret if you found yourself missing the beat of Dylan’s lead, there are many things a taxpayer can do to reduce capital gains tax, especially for self-created works of art. Here’s how.

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