Loopholes Archives - Page 2 of 13 - Think Outside the Tax Box

Loopholes

By Ted Stotzer

Selected Techniques to Monetize Tax Attributes

In the prior article "Tax Trends in M&A and What It Means for Your Clients," we had discussed certain techniques to, e.g., maximize net operating loss (“NOL”) and interest expense deduction utilization in the context of M&A transactions. This article examines certain additional strategies to monetize expiring, latent, or otherwise disallowed tax attributes.

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Popular Tax Shelter for the Ultra-Wealthy Comes onto the Radar

In a recent turn of events that has caught the attention of financial experts and policymakers alike, Senate Finance Committee Chairman Ron Wyden, D-Ore., has unveiled the results of an 18-month investigation into the use of Private Placement Life Insurance (PPLI) by the ultra-wealthy. The investigation, the first of its kind focusing on PPLI, highlights the use of these policies as a significant tax shelter mechanism, revealing the ways in which a small number of wealthy individuals are leveraging them to avoid substantial tax liabilities.

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TAX COURT ROUNDUP – September 2024

Much happening, even in August. This has hardly been a lazy hazy summer.

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The Hidden Benefits of Private Placement Life Insurance (PPLI) for High-Net-Worth Families

For wealthy families, the world of finance can feel like a high-stakes chess game. With increasing state and federal income tax rates, new tax laws on the horizon, and the complexities of private investments like hedge funds, finding ways to grow and transfer wealth efficiently is more important than ever. Enter life insurance—a tool not just for its traditional role of providing death benefits but as a strategic ally in tax-efficient wealth management. In particular, Private Placement Life Insurance (PPLI) offers unique advantages that make it a worthy consideration for those with sophisticated financial needs and significant liquidity.

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2024 Endless Summer Education BONUS Series Calendar

Our 2024 SUMMER EDUCATION SERIES was such a big hit that we've decided to bring you two BONUS webinars! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...

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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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Intentionally Filing a Defective Tax Return

Creativity on a tax return is a natural tendency. Many strategies and behaviors we know are wrong, e.g. not reporting all income. However, is it ever okay to disregard some deductions and pay more tax? At first glance, it would seem that the IRS should like the idea of more reported income and a higher tax liability attached to the additional income. The IRS does not.

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Loose Change in Your Couch and Maybe a Tax Break at Your Kitchen Table

A 2023 Tax Court decision upheld what many small business owners and tax practitioners have wondered about for some time. The court found that shareholders of an S corporation could exclude rental income paid to them by their S corporation for holding planning meetings in their homes. While the IRS and court found that the amounts charged by the shareholders were excessive, the court found the arrangement itself within the bounds of the law. This article examines this case and underlying law and when and how this is a planning idea worth pursuing, the limitations and unknowns involved, and the policy implications of this long standing exclusion. The case is Sinopoli, TC Memo 2023-105 involving the exclusion at IRC Section 280A(g).

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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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