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New tax reduction strategies carefully explained and exhaustively researched every two weeks. Receive breaking news updates on tax law changes. Members only monthly AMA with TOTTB.tax.

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How to Deduct Even More Expenses as Self-Employed Health Expenses

Question: Can I still deduct self-employed health insurance if my spouse has insurance through their employment? Answer: You may potentially qualify for the deduction even if your spouse has insurance through their employment. Healthcare costs seem to be always on the rise, and if you’re self-employed if can be tough to find an affordable option for a single participant plan. The good news is, the Self-Employed Health Insurance deduction provides an “above the line” write-off helping you not only save tax through a lower taxable income, but it also helps to slash your Adjusted Gross Income (AGI). Lowering your AGI also helps mitigate the disadvantages of AGI based tax laws. For example, some itemized like medical expenses and charitable contributions can be hampered by the amount of your AGI. In other words, AGI determines how much of certain deductions and tax credits you can take. There are three steps to qualifying for this deduction including some special provisions that let you sweeten the deal. Did you know you can even write off dental and long-term care insurance as self-employed medical expense? You can! Here’s how to get even more write-offs if you’re self-employed.

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CURRENT EDITION

2025 Tax Surprises You Shouldn’t Overlook

There are a few tax rules new for 2025 that may catch some individuals and their tax advisers by surprise. These changes have not received lots of attention either because they are overshadowed by related changes that are more significant, or they were enacted a few years back with a future effective date that arrives in 2025. This article covers changes for 2025 that you will want to be sure to share with clients to avoid surprises at a later date.

Leaving the United States, Part I: Expats

When Americans speak of leaving America, they generally are expressing a desire to live elsewhere in the world for cultural reasons or due to cost of living. These people are called expatriates, aka expats. For clarity, a mere visit to another country does not make you an expat. To be an expat, the move needs to be long-term and often includes working or retiring in the new country. Expats live somewhere outside the U.S., but still have a tax obligation to the U.S. and possibly the country they move to. That will be the focus of this article.

Tax Preparer Hit with Stiff Sentence

John Anthony Castro is a colorful character. He entered several Republican primaries seeking the Presidential slot after failing to win the primary for a Senate seat representing Texas. He sued to have our once and future President Donald Trump be removed from the ballot on Fourteenth Amendment Section 3 grounds. As we can easily infer, those suits went nowhere. But more than anything, John Anthony Castro was a tax guy with a virtual practice with locations in four cities. Not anymore. Now he is resident in a Bureau of Prisons facility – the Federal Medical Center Fort Worth. On October 30, 2024, Judge Terry Means sentenced Castro to 188 months in prison, followed by one year of supervised release and restitution of $277,243, following his conviction on 33 counts of “Aiding and Assisting in the Preparation and Presentation of a False and Fraudulent Return.” Does the sad story of John Anthony Castro hold any lessons for us? Perhaps.

SIMPLIFIED TAX STRATEGIES &
PRACTICAL IMPLEMENTATION

Think Outside the Tax Box provides tax reduction strategies along with practical
implementation advice in order to reduce your clients’ federal tax bill with ease.

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