Yet Another Proposed Listed Transaction – CRATs and Annuities

Compliance, Income Tax, Regulatory, Tax Controversy

On March 25, 2024, the IRS issued Prop. Reg. Section 1.6011-15[1], which designates certain transactions involving charitable remainder annuity trusts (“CRATs”) in tandem with single premium immediate annuity (“SPIA”) products as listed transactions[2]. Last year, I wrote an article in which the Tax Court decided against a taxpayer couple who undertook this exact transaction.[3] Now,…
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Successor Trustee Liability for Unpaid Estate Tax

Cases, Court of Appeals, Estate Administration, Estate and Gift Tax, Estate Planning, Fiduciaries, Tax

In a previous writing, I discussed the potential of an executor to be personally liable for a decedent’s tax obligations.[1] That discussion was based on lessons learned from a Tax Court opinion,[2] outlining certain steps for executors to consider in minimizing exposure to such personal liability. In 2023, in a split decision, the Ninth Circuit…
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Monetized Installment Sales – Proposed Regulations will Lead to Burdensome Reporting Requirements and Increased Scrutiny

Business Transactions, Compliance, Estate Planning, Income Tax, Regulatory, Tax, Tax Controversy

Monetized Installment Sales, as previously written upon by Gray Edmondson,[1] have been subject to increased scrutiny by the IRS in recent years, making its “Dirty Dozen” list in each of the last three years.[2] The IRS remains on the offensive in scrutinizing such transactions, issuing proposed regulation under Internal Revenue Code Section 6011 in August…
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Executor Liability for Decedent’s Tax Obligations

Cases, Estate Administration, Estate and Gift Tax, Fiduciaries, Tax, Tax Controversy, Tax Court

A recent Tax Court opinion[1] highlights one of the risks of serving as executor or administrator of an estate, potential liability for a decedent’s tax obligations. The case involves application of the federal priority statute[2] applicable to fiduciaries.[3] That statute provides, in relevant part, that “a representative of a person or an estate (except a…
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