Loopholes Archives - Page 11 of 19 - Think Outside the Tax Box

Loopholes

By Peter J Reilly CPA

When Debts Go Bad: The Challenges of Deducting Delinquent Debts

It is painful when you finally realize that the money you expected to be repaid is never coming back. The tiny silver lining in that cloud might be the tax benefit of “writing off” the debt. Unfortunately, that silver lining may well be eclipsed by an even bigger cloud. Writing bad debt off is not that easy, and there’s probably no silver lining to that cloud. Ironically, you might find that the mistakes that caused you to be holding a bad debt might be what prevents you from getting a usable deduction.

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TAX COURT ROUND-UP JULY 2023

Here's the latest filings and tax court cases for July, 2023!

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Tax Court Roundup June 2023

This month I've decided to change format. I'm grouping Tax Court thumbnails by category. Not every reader deals with every issue. But coverage is still useful even where only a few specialize. Click here to read the latest happenings!

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Famous Bad Citizens and the Code That Caught Them – Al Capone

At its peak, Alphonse (Al) Capone’s criminal empire was worth approximately $1.3 billion when adjusted for inflation. On June 5, 1931, Capone was indicted on multiple counts of income tax evasion. At the time the maximum penalty for his offenses was 32 years in jail and $80,000 in fines (almost $1.6M in inflation adjusted dollars). The prosecution in Capone’s case “documented Capone's lavish spending, evidence of a colossal income. The government also submitted proof that Capone was aware of his obligation to pay federal income tax but failed to do so." Click here to keep reading about this fascinating case…

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Tax Court Roundup – May 2023

As always, much has happened in the tax courts this past month; let's jump right in!

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Key Lessons from 2022 Tax Rulings

This article does not summarize key rulings of 2022, but instead offers some key lessons and reminders from 2022 tax opinions as well as a few IRS rulings. If you want to read the ruling, see the citations and links. Takeaways from a few state tax rulings that have a lesson of relevance beyond the particular state are also included...

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2023 Summer Education Series Event Calendar

We are so excited to announce the 2023 Summer Education Series! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax! Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...

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TAX COURT ROUNDUP – April 2023

Another active month, with plenty of variety and practice tips. And new Tax Court Rules announced...

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How Should a Disregarded Single Member LLC File a W-9?

Although Form W-9 has some other purposes, a company will usually ask you to fill it out if you are a business-to-business service provider . If you don’t provide a TIN to your customer, they may have to subject you to backup withholding . If it is my company that asks you for the W-9, I am not going to do backup withholding if you don’t send me the W-9. I’m just not going to pay you until you cough it up. I believe in learning from experience. But it is better if the experience you learn from is other people’s experience. That is why a very large percentage of my tax writing is from court opinions, most often the United States Tax Court. This piece is my own experience.

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