Captive Insurance Tax Deductions Denied, No Risk Distribution

Insurance premiums go up and then they go up some more. The amounts can be substantial. This is particularly true for businesses that offer insurance to employees or that insure more types of risks. And many business owners note that while they pay substantial insurance premiums, the insurance companies often do not have high payouts.……

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Court Limits Equitable Tolling For Late Tax Court Petitions

We live in a fast-paced world where technology has made it possible to do more, see more, and accomplish everything else more efficiently. While some routines of life have not changed, most have been transformed by our increasingly connected environment. For better or worse, one thing that has not changed is the concept of deadlines,……

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Split-Dollar Insurance Failure: Income and No Tax Deduction

Business owners frequently seek ways to maximize tax deductions while providing benefits to key employees. Life insurance arrangements can play a part of this strategy. Life-insurance related strategies can be particularly useful if they come with significant tax advantages and help the parties meet their financial goals. However, the line between legitimate business expenses and……

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Business Advances in Revenue-Sharing Deals Not Deductible

Government agencies and non-profits often enter into business arrangements with private companies that, ultimately, are structured as a percentage of revenue. This approach frequently replaces traditional fixed payments like rent or management fees. The typical example involves a building that a business owns and leases to a government agency or non-profit. The business collects a……

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Probate Estate Can Serve as a Condit for Retirement Assets

When estate planning involves retirement accounts, most advisors recommend naming beneficiaries directly to avoid probate delays and preserve tax advantages. Surviving spouses typically receive the most favorable treatment under the tax code, with the ability to roll over inherited retirement assets into their own accounts and defer distributions based on their own life expectancy. However,……

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Settling Tax Debts Based on “Future Income” for Business Owners

The IRS settles balances for back taxes for less than what is owed through the “offer in compromise” program. The idea of this program is to allow taxpayers to have a so-called “fresh start” when they get really behind. This way the IRS collects something rather than nothing. Those who work as employees are less……

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Sidestep Tax Court Review by Applying Overpayments

What happens when a taxpayer properly invokes their right to challenge the underlying tax liability through the CDP process, but the IRS then uses subsequent overpayments to zero out the disputed balance? Can the IRS effectively eliminate tax court jurisdiction by manipulating these overpayments mid-process, leaving the taxpayer without any forum to resolve their legitimate……

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