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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Intentionally Defective Grantor Trusts – Have your cake and eat it, too

Shortly before his passing, Benjamin Franklin uttered one of his more infamous quotes, “In this world, nothing is certain except death and taxes.” With the certainty of death implicitly comes another: everyone will transfer his or her wealth, whether in life or after death. How a person transfers wealth will affect how the other certainty,…
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IRS Reverses Position on Modifying Irrevocable Grantor Trusts

The Internal Revenue Service (“IRS”) issued Private Letter Ruling (“PLR”) 201647001 in November of 2016, in which it took the position that a modification to an irrevocable grantor trust to add a discretionary income tax reimbursement clause did not change the beneficial interests in the trust, and therefore did not result in a gift, because…
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