Loopholes Archives - Think Outside the Tax Box


By Lewis C. Taishoff


A very mixed bag this month: IRS shifting ground on the eve of trial, plenty of discovery, loyalty programs, the end of the road for meaningful Section 6751(b) supervisory approval, and arrival of a new Special Trial Judge. And, as always, a lot of questions.


Can You Write Off Your Vacation on Your Taxes?

I saw a meme that said, “accountants go on vacation just so they can work from another location.” This might be true. So maybe, just maybe you can write your vacation off on your taxes. But on a serious note, this is a question that taxpayers have. “Can I write off my vacation on my taxes?” I hate to blame everything on the internet but...it is a dangerous place for taxpayers. There is an infamous Tik Tok video turned reel that has found its way into my DMs and e-mail inbox several times. I’m often amused by the bad tax advice that goes viral online. The comments tend to make me giggle or give me cause for concern. This particular video gave me more cause for concern. The main reason it did this is because of the amount of tax professionals that shared in agreement. I’m all for advertising on social media but often we must be careful as tax professionals. We have certain ethical obligations that unfortunately do not apply to other industries. We do not want to mislead taxpayers for “likes” or potentially going viral. Let me get to the details of the video. A tax professional whose credentials I won’t mention, was sharing how taxpayers can use their entire family vacation as a write off on their Schedule C. Rightfully so, this made taxpayer’s ears perk up. Why not kill two birds with one stone, right? What should not have happened was tax professionals sharing the video with filling in the blanks. I know you would never do that, and that’s why you’re here. To find out what parts of travel your client can write off on their taxes. So, let’s look at what constitutes something being a business expense. Then we’ll look at the due diligence you should take to make sure their travel and meal expenses are legitimate.

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The latest Federal Tax Court news, updates, and hot topics!

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Beyond The Returns – Live Webinar Series Event!

Tax season is always demanding. But what comes after? As a dedicated tax professional, it's crucial to continually enhance your practice and adapt to an ever-changing landscape. Introducing the Beyond the Returns Series – an in-depth suite of four live webinars designed to transform your firm's future. Led by industry veterans, Amber Gray-Fenner, EA, NTPI Fellow, USTCP and Matt Metras, EA, this series promises actionable insights to ensure you're well-prepared for the 2024 filing season and the years to come. Don't miss out on this opportunity to redefine and rejuvenate your tax practice.

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TAX COURT ROUNDUP – September 2023

This roundup will spend a lot more space than usual on one story, because it’s the biggest of the year in Tax Court so far...

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Tax Court Roundup – August 2023

The dog days, the doldrums, the get-out-of-town days...they're here. The United States Tax Court is not immune, as the blockbuster cases and newsletter headliners have largely vanished. Still, there are report-worthy stories, despite the call of seashore and mountain meadow.

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Cautions in Tax Research — Finding True Guidance

The tax research process continues to grow increasingly complex for numerous reasons. This article notes several of these reasons and offers tips for your tax research process to be sure you have the latest appropriate guidance for answering tax questions and taking properly supported positions on tax returns.

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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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