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Personal Liability for NY Sales Taxes –Sometimes, There’s No Denying It

It wouldn’t be far-fetched to say that, as a species, we humans have a propensity – rooted in our instinctive tendency for self-preservation – toward denying anything we believe may cause us harm. It should come as no...more

Related Party Transactions Converting Gain Into Ordinary Income – Be Careful Out There

To avoid the manipulation of tax consequences to which transactions between certain related taxpayers may be susceptible, the IRS and the Courts generally require that such transactions be closely scrutinized to ensure that...more

LLC as S Corporation: Square Peg Meets Round Hole?

At different times over the course of the last thirty days or so, I have seen reports describing various plans to increase income taxes and/or wealth taxes on the “rich” that have either been endorsed or proposed by the likes...more

Shared Appreciation Interest: Debtor-Creditor or Partners?

When is a loan not a loan? When it’s something else – for example, equity. This is one of those pesky facts and circumstances issues that plague courts, taxpayers, and tax advisers to no end. Debt- On one end of the...more

Moving to the U.S.? Have You Planned for the Estate and Gift Taxes?

It is a fact that the phenomenon of human migration has been a major force in the history of the world. Indeed, among the themes that have remained constant during my years of practice, there are two that may be...more

Planning for the Interest Charge on Installment Sales: Decanting a Grantor Trust?

I recently encountered an interesting situation in which someone suggested that a grantor trust be decanted into a non-grantor trust before the end of the taxable year. The reason? To avoid the special interest charge that...more

The Transaction That Failed – Tax Treatment of Termination Fees

Deal Costs, Generally- Every purchase and sale of a business, whether from the perspective of the seller or the buyer, is about economics, and few items will impact the economics of the transaction more certainly or...more

Either An Investor or a Dealer Be – That is the Question

The Housing Market- During the first quarter of 2022, the housing market accounted for 16.7 percent of gross domestic product (“GDP”). This figure represents a return to historic norms following the substantial reduction...more

An S Corporation’s Sale of Real Property Following the Death of Its Shareholder

Don’t Do It- There are certain generally accepted “dos and don’ts” of which almost every investor is certainly aware. For example, do not put all your eggs in one basket; if an investment seems too good to be true, stay...more

Will New York Be Looking At Your Federal Tax Return? Probably

State Finances- Much has been written over the last few weeks about the unprecedented financial cushion that many states have accumulated thanks to federal support prompted by the pandemic and larger-than-expected tax...more

The Rental of Art Between Related Parties: Applying the Resale Exclusion to the N.Y. Sales Tax

“Yes” to Art, “No” to Tax- Private patronage of the arts. For centuries, artists, museums, and galleries have depended, in no small part, upon the largesse of wealthy families. Today, as in the past, many of these...more

Me, Myself, and I: Tax Liabilities and Dealing with One’s Own Business

“It’s My Business”- The owner of a closely held business will often find it difficult to distinguish the business from their own person. That is certainly true for a sole proprietorship. In many cases, unfortunately, the...more

Deferring the Tax Hit on a Grant Equity to an Employee – Are You Prepared to Enforce the Forfeiture Provision?

“Would I ever leave this company? Look, I’m all about loyalty. In fact, I feel like part of what I’m being paid for here is my loyalty. But if there were somewhere else that valued loyalty more highly, I’m going wherever they...more

New York’s Pass-Through Entity Tax, F Reorgs, and the Sale of An Electing S Corp

Timing- I had planned to post this piece during the third week of December, a day or so after the exchange between Senator Manchin and the White House sealed the fate of the Build Back Better plan, at least in its current...more

Gift Transfers: Not on the Congressional Agenda, But Still in the Crosshairs of the IRS

Same old in D.C.- On Monday, November 15, the President will sign into law the approximately $1 trillion Infrastructure Investment and Jobs Act that was finally passed by Congress when the House approved the Senate’s...more

Selling to Private Equity? Maybe You Should “F Reorg” First

Having Fun? Hope you had a decent weekend. Perhaps you did something interesting, maybe even fun, like some end-of-season apple picking? Or maybe you had a cider donut with some hot coffee at a farm stand you stumbled upon...more

Maybe Tax the Rich, but Not The Conversion of S corps into Partnerships – What Gives?

Tax the Rich? A few days ago, an opinion piece that appeared in the Wall Street Journal began as follows: “President Biden’s effort to pass the largest tax increase in U.S. history is based on the verifiably false...more

Disposing Of Assets Under The Ways and Means Committee’s Proposals

First Step- Last Wednesday, the House Ways and Means Committee approved that portion of the 2022 budget legislation with which it was tasked by the Congressional Budget resolution of August 24. The text of the bill...more

Tax Distributions As Fraudulent Conveyances?

The Calm Before? I’m confused. For better or worse, I’m pretty sure that I am not alone. Last week, in a letter addressed to the American people, forty-six of the fifty Republicans in the U.S. Senate indicated they...more

Capital vs Ordinary Loss When An Investment Goes South

Capital Loss- If the amount realized by a taxpayer upon the sale of a partnership interest to a third party is insufficient to restore to the taxpayer their adjusted basis for the interest – i.e., their unrecovered...more

Biden’s 2022 Revenue Proposal, Profits Interests, And The Alchemy Of Compensation

Recap- Last week, we considered several of the revenue proposals included in the Biden Administration’s 2022 Budget that are probably of interest – or should we say, “of concern”? – to the owners of closely held...more

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