All Articles - Think Outside the Tax Box

CURRENT EDITION

By Jeff Stimpson

How to Deal with Huge Tax Debt

The only thing scarier than owing Uncle Sam a lot in taxes is being unable to pay the bill. Luckily, the Internal Revenue Service has ways for you to whittle what you owe. Just make sure which method works for you, depending on such factors as the size of your tax debt and what you can afford to pay and when. Don’t panic. Here’s how individual taxpayers can proceed – and what to watch out for.

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Way Out of State Tax on Student Debt Forgiveness

There was some rain on the parade of celebration of the student loan debt forgiveness. The Tax Foundation, perhaps with a touch of schadenfreude, announced that the forgiveness, not federally taxable due to recent legislation, might be taxable in as many as thirteen states. They have taken a closer look and backpedaled quite a bit. It is now down to four states Minnesota, Mississippi, North Carolina and Wisconsin and those are not for sure. But, there is likely another way out for many of the recipients of this boon. Keep reading to learn more!

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Fully Funding Your HSA

It's 4th quarter, soon taxpayers will be reaching out to their trusted advisors. They will want to see what they can do last minute to save on taxes. There isn't much you can do at the end of the year. Still, these taxpayers will reach out expecting you to wave a magic wand and save them a few thousand dollars. Well, this year you may be able to do just that. Even if they have already maxed out their retirement accounts. Taxpayers are not restricted from using this strategy by income or self-employment. Are you ready to add this triple tax advantaged savings tool to your bag of resources?

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Client Alert

Live Event! Reasonable Compensation for S Corps Webinar

A TOTTB Live Webinar Event sponsored by our friends at RCReports! For two decades the IRS has been preparing an assault on reasonable compensation for S Corps. Their arsenal is now fully locked and loaded. In it, there is everything from commonsense tools to obscure memos. We will explore key court cases, IRS guidelines, preparer penalties and some of the obscure weapons the IRS has put in place. We debunk common myths and fiction on how reasonable compensation should be calculated and replace it with facts and methodologies that the IRS relies on.

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Tax Disaster Relief – More Than Just Return Extensions

Evie and I withdrew from active tax practice in 2018, but she maintains a sort of family and friend's freebie practice using Drake. I help a little. We have been struggling with difficulty getting the information for one of our “clients” as we watch the ultimate October 15 deadline creeps up on us. She is in Florida in one of the counties covered by President Biden’s disaster declaration relative to Hurricane Ian. So it was sort of a relief to find out that we have another three months to get the return done. In this case it is not a huge benefit since interest will still clock if there turns out to be a balance due, since the payment was due on April 18. “Certain deadlines” falling on or after September 23, 2022 and before February 15, 2023 are postponed through February 15, 2023. Read on to learn more!

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Is a Self-Directed Crypto IRA a Good Idea?

Self-directed IRAs (SDIRAs) have long been a vehicle for less traditional investments that can't be held in a normal IRA, such as precious metals, real estate, or tax liens. Cryptocurrency is the newest addition to that list of alternative retirement savings and has exponentially grown in popularity in recent years. The rules governing SDIRAs are complex, and taxpayers can easily and unknowingly violate the rules, resulting in the entire IRA being deemed distributed and potentially subject to tax. As the famous adage says, "with great [investment] power comes great responsibility." Keep reading to learn more!

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Just Good Business – Review and Shop Your Financial Accounts

The fourth quarter just started and it's time to have your clients take a look at their financial services game plan. With interest rates approaching historic highs now is the time to review financial accounts to ensure high returns on cash investments, optimize reward-bearing accounts, and minimize interest paid and fees for financial products and accounts. The goal of this review is to ensure that investments and rewards programs are tuned for optimal results and to minimize interest and fees throughout next year. I won’t be providing much in the way of specific, prescriptive advice. I am not a registered investment advisor or a certified financial planner, nor do I recommend specific products, services, or institutions (other than a subscription to this publication). Rather, I will be providing a framework for the review, encouraging you to ask good questions about the goals for the various accounts, and reminding you to consider the big picture as well as the role each part plays in it. Let’s get started!

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How to Avoid Losing Valuable Noncash Charitable Contributions

The rules for noncash charitable contributions defy easy summary. On the other hand, they are not rocket surgery. Moving on from the humor, if you want to sum them up in a sentence you can use Reilly’s Seventh Law of Tax Planning: Read the instructions. Specifically, you want to read the instructions to Form 8283 Noncash Charitable Contributions. There is, of course, more to it than that, but you will find a remarkable number of disallowed deductions from not following those instructions. To be fair, sometimes there are other shenanigans going on and the instruction failures are the easiest way for the IRS to attack. Nonetheless, there is nothing to say that the IRS will not use the precedents set in those cases on your client even though they are not trying to get away with anything. To get a simplified list of what to know and implement, continue reading.

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Should Your Practice Use a Client Portal?

You may know me as the “crypto guy” here at Think Outside the Tax Box. It might seem like that’s all I ever write about. But this time, I’m sneaking an article in while my editor is on vacation. Because I want to talk about using a client portal and why all tax professionals should be using one in their firms. Some firms may have dipped their toe into the digital waters out of necessity as a by-product of the pandemic. Others may have started the process long before Covid existed. According to a completely unscientific poll I ran on Twitter, 70 percent of firms are still processing returns at least partially on paper. This can mean either receiving paper documents from a client or delivering a hard copy of the completed return to the client. As the numbers from a Twitter survey are clearly biased toward firms already comfortable with digital technology, we can safely assume more accurate numbers are significantly higher. Since TOTTB refuses to provide me with a budget to run a full, comprehensive study, we’ll just have to run with my perfunctory data as well as published data from a poll Canopy conducted in 2021. Canopy surveyed more than a thousand small businesses and found that 63 percent admitted that their accountant did not offer any portal. More surprising, depending on whom you ask, is that more than two-thirds of respondents said they would be interested in switching to an accountant that allows them to use photos of their documents for easy sharing. While I’m not here to debate the issues of opening a gajillion .jpg files and how that might negatively affect my practice, the impact of using technology can improve your efficiencies, communications, and improve your workflow. To learn how, continue reading.

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