Goodbye, Chevron – Loper Bright Enterprises

As tax planning practitioners, we do not typically see issues we deal with daily become the subject of cases before the United States Supreme Court. This term, we had the Connelly[1] case involving estate tax valuation of a decedent’s stock in a corporation funding a redemption buy-sell with corporate-owned insurance. Shortly thereafter, the Supreme Court…
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The Often-Overlooked Benefits of Qualified Small Business Stock

If you started a business organized as a C corporation, you may be able to avoid some, and possibly all, tax liability when you sell the stock of the C corporation. As previously written upon by Gray Edmondson,[1] Section 1202 of the Internal Revenue Code (“Code”) provides for the exclusion of gain on Qualified Small…
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Revisiting Intrafamily Loans – Bolles

The Ninth Circuit Court of Appeals recently affirmed a Tax Court opinion dealing with the effect of lifetime transfers by a mother (Mary) to her son (Peter).[1] At issue was the nature of those transfers. On the one hand, Mary Bolles and her estate argued that the transfers constituted loans from Mary to Peter. On…
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Yet Another Proposed Listed Transaction – CRATs and Annuities

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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Excluding Gain on the Sale of Your Principal Residence

Under IRC §121, gain on the sale of a principal residence of up to $250,000 (or $500,000 for spouses, see below) may be excluded from gross income. This may seem pretty straightforward, and many times it is, but it also has numerous requirements in order to apply, as well as numerous exceptions that may apply.…
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Successor Trustee Liability for Unpaid Estate 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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The 2024 Dirty Dozen – The IRS’s Annual Warning

Every year, the Internal Revenue Service (“IRS”) releases its “Dirty Dozen.” The Dirty Dozen, as written previously about by my colleague, Devin Mills,[1] is a list of twelve prevalent scams the IRS bodes taxpayers to be weary of during tax season, as they “put taxpayers, businesses, and the tax professional community at risk of losing…
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Estate Planning with Partnership Interests: Income Tax Considerations

Small businesses predominate the United States.[1] Many of those businesses operate through entities taxed as partnerships.[2] Those entities may be general partnerships, limited partnerships, LLC’s, or other state law entity types.[3] Many partnerships are formed as part of family and estate planning. Some benefits of the use of partnerships in estate planning include, but are…
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Insurance Arrangement Found to be Split Dollar Insurance Arrangement

Split dollar life insurance arrangements can take on a number of forms, and the exact structure of the arrangement determines the tax consequences, which can become complicated quickly. In a recent case out of the District Court of Ohio, the court held that an insurance arrangement between a single member C corporation, Peter E. McGowan…
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ETA 2026 – Switching from Inclusion to Exclusion Planning for the Estate Tax

Currently (and since the Tax Cuts and Jobs Act of 2017), we, like many other practitioners, have seen an incredible uptick in inclusion planning[1] instead of the traditional exclusion planning (getting assets out of one’s taxable estate). A primary driving force for this major shift was the essential doubling of the estate tax exemption (from…
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Directions

[**Practice Alert: Corporate Transparency Act is Here: What You Need to Know**](https://esapllc.com/practice-alert-cta-mar-2024/)
[**Practice Alert: Corporate Transparency Act is Here: What You Need to Know**](https://esapllc.com/practice-alert-cta-mar-2024/)