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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Charitable Deduction Rules – No Excuses – Acknowledgements

There is a story I heard even before I started doing tax work when I was a hotel night auditor. It was about a guy named Joe who ran a luncheonette where he also sold newspapers and candy bars and the like. Joe’s Place was across the street from Our Lady of Perpetual Responsibility, a Catholic parish. Joe would see Father Mulcahey carrying a heavy bag every Monday morning. The good father was heading to the bank with the Sunday collection. One day Joe invited him in for a cup of coffee and proposed a win/win. Joe was always running out of change on Sundays. So how about if Father Mulcahey has the ushers count the coins and bring them over, Joe would write a check for the coins, and the father will just have Joe’s check to bring to the bank on Monday? Then, Joe would deduct the check written to the church as a charitable deduction. It was a great plan and it worked well for several years until the IRS audited Joe and a skeptical IRS agent called on Father Mulcahey about Joe apparently being Our Lady’s biggest donor. After all, he had the canceled checks. So if a canceled check to church on Sunday won’t work to document your charitable deduction, what will? Keep reading to find out!

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Who You Gonna Call? Not the IRS – A Guide to IRS Online Tools

You don’t have to be a tax geek to know the IRS has trouble picking up the phone. Old habits die hard. If you have a tax question, what do you do? You call the IRS. Good luck with that. You’ll be on hold for a long time if you can get through at all. The IRS initiated a call-back feature, but it’s not always available. The hold music is uninspiring; sometimes, after holding for hours, you get the dreaded “courtesy disconnect.” Yikes! Let’s face it. The IRS has a full plate; years of doing more with less have crippled the agency. Congress is quick to excoriate the IRS for poor service but keeps piling on more tasks (without necessary funding). Luckily, the IRS is working hard to provide more and better online applications and resources. There’s a lot out there, some well-known, some not so well-known, click here to take a tour and discover which shortcuts will help you most.

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Client Alert

Self Rental Tax Dilemma: Are Your Deductions at Risk?

It’s challenging at times to understand the passive activity loss guidelines. Many taxpayers are not fully aware of the rules or how they could affect investments and transactions. There are some details that, if not taken care of in advance, could have serious detrimental tax effects. The way to handle self-rentals in relation to the passive activity loss rules is one of these subtleties. Although many professionals know the self-rental regulations, there are some circumstances that can result in a loss of desired tax benefits. To continue learning about a general overview of the self-rental provision and the passive activity requirements and how to maximize your deductions from them, keep reading. You will also learn the effects of selling an operating company with a self-rental property still on the books.

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Just Good Business – Review Your Office Security

Office security. It’s for you and your small business clients. Sometimes small business clients who have relatively low-tech operations don’t think they need to think much about office security. That’s just not true. Almost every small business has some level of liability exposure for theft of client information or their own information (banking, credit cards, account passwords, etc.)—even businesses that don’t consider themselves “web based” or “high tech” may have client or company proprietary information they want to keep secure and private. Often business owners focus on cyber security (and with good reason). But a good, comprehensive security plan creates a safety triangle around important information and the property that holds it. The three sides of this triangle are cyber security, physical security, and (at the base of it all) operations security. Keep reading to secure your future!

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The Inflation Reduction Act Town Hall

We’re hosting a live open discussion forum to help educate you on the new Inflation Reduction Act! The recently passed Inflation Reduction Act (IRA) makes some big promises: lower energy costs, provide tax credits for electric vehicles, negotiate cheaper medications for seniors, deliver faster tax refunds, and create more responsive IRS agents! How all these promises are paid for and how they impact the average American are already the topic of intense debate and, in some cases, the cause of outright fear! In fact, there has been so much concern and debate around this new bill that we’ve decided to hold a town hall on the subject! Keep reading to get all the details...

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10 Reasons Your Clients Should Get a Tax Divorce

As a married individual, you can select a tax filing status as either married filing jointly or married filing separately, and in some cases neither of these statuses achieve what is possible for two single taxpayers each filing their own tax return. In many cases it can seem you are getting penalized for being married in the U.S. You may get frustrated that you seem to keep getting hit with “wealth taxes or penalties.” Of course, you may not refer to it that way. But when you see things like the Alternative Minimum Tax, The Net Investment Income Tax, the Additional Medicare Tax, and a whole variety of other taxes that are higher for married filers than they are for two single people…you may be tempted to think about a divorce. And “live in sin”? No matter your personal beliefs there are at least 10 tax attributes that cost married filers more than two single people. In some instances, children are in the mix, as they relate to specific credits. Some of these situations only apply to wealthy couples. Some only apply to those earning $50,000 or less or seniors. These attributes, commonly known as the so-called “marriage penalty” refer to situations where it may pay to file as two single individuals rather than as a married couple. However to qualify, you cannot legally be married as of December 31. To learn more about these penalties and find out how to work around them, continue reading.

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Retirement Tax Planning – Having a Rough Year? Turn Lemons into Lemonade by Using Business Losses to Offset Roth IRA Conversions

A ROTH conversion can be a very powerful tool for your retirement. While you don’t receive a tax break for deposits to your ROTH account, qualified withdrawals from the account are tax-free, even earnings. This is an excellent way to avoid tax increases. Let’s say your taxes rise due to increases in tax rates, or because you earn more, which catapults you to a higher tax bracket, ROTH IRA conversions can save you a ton of money in taxes over the long term. The disadvantage, of course, is that tax is due on the amount you convert based on the value at conversion. But many times, such as when you are in a temporarily low tax bracket, have large deductions during the year, or in a year with business losses, can provide optimal opportunities to convert with little to no tax expense. Looking for more strategic times to convert? Keep reading to learn more.

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Client Alert

TAX PLANNING – IT’S NOT JUST FOR THE WEALTHY – Part 2

In Part One of this series, we looked at strategies to reduce adjusted gross income (AGI). But the planning doesn’t stop there. We call deductions that reduce AGI “above the line” deductions. But wait, the tax saving opportunities don’t stop with AGI. Even with the higher standard deductions courtesy of the Tax Cuts and Jobs Act (TCJA), there are many opportunities for taxpayers of modest means to find “below the line” tax savings. Let’s explore the many ways you can reduce your taxable income and whether you maximize your tax benefits even more with tax credits. Keep in mind that a tax deduction reduces your taxable income A tax credit reduces your tax dollar for dollar and, in some cases, the credits are refundable, meaning you can get additional tax benefits even after reducing your taxable income to zero . Read on for some tax planning tips reducing taxable income and maximizing credits that may work for you.

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