Feature Article Archives - Page 10 of 13 - Think Outside the Tax Box

Feature Article

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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Deducting Business Meals and Entertainment: The good, the bad, the very recently changed

“Say dog.” My dad once told me that a friend paid for his lunch and said, “Say dog, then I can write this off.” She bred show dogs. File that under “nope.” That is not how the meals and entertainment (M&E) deduction works. Not even before the Tax Cuts and Jobs Act (TCJA) changed the rules. The deduction for M&E is a favorite of many of our clients and rightfully so. Nevertheless, it can be a fraught area if taxpayers and their advisors don’t have a comprehensive understanding of how the rules for deducting expenses apply across the many different scenarios in which our clients are likely to apply them. The IRS issued the final regulations for deducting M&E expenses under Internal Revenue Code (IRC) § 274 on October 9, 2020. It made some additional, short-term adjustments when the Consolidated Appropriations Act (CAA) became law on December 27, 2020. Here is an overview of the new regulations, how to use them to your clients’ benefit, and how to avoid the most common pitfalls.

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How to Turn a 1031 Real Estate Capital Gain Into a Passive Investment

You may be familiar with the concept of a 1031 exchange as a way to defer gain on the sale of rental or investment real estate. But what happens when you want to completely exit the real estate game? A 1031 Exchange may not be the best option for you. There are a few drawbacks associated with a 1031 exchange, including the limited time frame you must acquire the replacement property, and that you must continue to invest in real estate. If you’re looking to continue deferring current or previously exchanged gains, a Delaware Statutory Trust (DST) may provide a solution to these issues. But investing in a DST property or properties is like any investment. It comes with its own risks and rewards. Read on to find out more.

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Hire Your Kids and Save Money on Your Taxes

Whether you’re preparing to have kids in the future or already have kids, there are tax strategies available (but often overlooked) that you should take advantage of. These are proven ways to save you money on your tax return. How do I know? Well, I use them myself. Bringing children into this world is a great joy and brings immense satisfaction. It’s important to remember, though, having children is a significant responsibility you should take seriously. From a very early age, you need to begin planning for your financial future to ensure you care for your children. There are 10+ unique ways the wealthy families in this country use their families to “qualify” for deductions that often go unused by the middle class. They go unused, not because the middle class can’t qualify; it’s that they don’t make the time to take proactive steps to prepare themselves. Here are just a few of the things you should know as you begin tax planning for your family.

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How to Do a Backdoor Roth IRA (Safely) and Avoid the IRA Aggregation Rule and Step Transaction Doctrine

The basic concept of the “backdoor Roth IRA contribution” is relatively straightforward. Contributing directly to a Roth IRA is restricted for higher-income individuals; once a married couple has an AGI in excess of $193,000 (or $131,000 for an individual), the maximum contribution limit to a Roth IRA reduces to zero. However, anyone with earned income can contribute to an IRA, regardless of how high their income is; at worst, higher income levels may limit the deductibility of that IRA contribution (for those who are an active participant in an employer retirement plan), but not the ability to make the IRA contribution. In addition, under the Tax Increase Prevention and Reconciliation Act of 2005 (TIPRA), there have been no income limits on Roth conversions of traditional IRAs since 2010. As a result, anyone who has funds in a traditional IRA, whether originally deductible or not, is eligible to do a Roth conversion. In other words, while income limits remain on Roth contributions, there are no income limits for a Roth conversion.

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Get Automatic, No Questions Asked Penalty Relief

The IRS loves to issue penalties to taxpayers. In fiscal year 2019, the IRS imposed a whopping $40.5 billion in civil penalties.1 If a taxpayer wants to contest an IRS penalty, it usually takes a really good explanation plus a lot of time and effort. However, there is a little-known IRS policy that allows a taxpayer to get penalty relief with no explanations required. Taxpayers who file returns late can quickly rack up huge penalty bills.

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More Cash Available for Employers Under Refundable Tax Credit

As 2020 winds to a close, we have seen many beneficial programs provided by the Coronavirus Aid, Relief, and Economic Security Act (CARES Act) and the Families First Coronavirus Response Act (FFCRA). While most media coverage has focused on loans to employers such as PPP and EIDL, it is important to remember some of the lesser covered programs also included in the tax relief programs. In fact, eligible businesses may qualify to get cash back in some instances. The employee retention credit (ERC) under the CARES Act offers a refundable payroll tax credit for certain wages and health plan expenses paid by businesses during the economic hardship. However, many business owners have uncertainty as to how to qualify when they have also received a PPP loan. The paid sick leave and paid family medical leave credits also offer a refundable tax credit for qualifying wages and Medicare tax and health plan expenses. These refundable tax credits are stackable for maximum benefit when used correctly. Read on to discover how to qualify.

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Year-End Tax Strategies for the Investor

The end of the year is a time for holidays, family, and maybe overindulging at the dinner table. It can also be a time for substantial tax savings. There are many techniques a taxpayer can use to minimize their tax burden for the year. The key to many of them is acting before the calendar year comes to a close. Specifically, let’s examine tax strategies for the taxpayer with investments, such as stocks, bonds, and mutual funds. These strategies can help taxpayers lower taxes, keep more money in their pockets, and donate to their favorite charities.

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How to Pay Less Tax on S Corporation Distributions

Most taxpayers understand that having an S corporation often eliminates the so-called “double tax” issue C corporations pose. However, the majority of S corporations begin as C corporations and the activity that occurred during the time it was a C corporation will determine how and when to tax distributions from the S corporation. C corporations cannot avoid double taxation on profits simply by electing to be treated as an S corporation (yet there are many other ways to save this double tax on C corporations, stay subscribed to learn about them). Withdrawing C corporation profits even when it later becomes an S corporation can create an extra tax. Here’s how to avoid that.

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