Jeff Stimpson, Author at Think Outside the Tax Box

AUTHOR SPOTLIGHT

Jeff Stimpson

Jeff Stimpson has been writing on tax and finance for 25 years, most recently for Accounting Today, Financial Advisor magazine and Insight magazine of the Illinois CPA Society. His other credits include accounting newsletters and blogs and articles for Intuit, among many others, covering sales tax, technology and practice management.

A native of Maine and author of Alex: The Fathering of a Preemie, he lives in New York with his wife Jill.

READ MORE BY Jeff Stimpson

When Does Married Filing Separately Make Sense?

If your clients are married, at this time of year they’re probably choosing to file their taxes under the status of Married Filing Jointly. But is MFJ the best move? Married folks have other options; one of them is Married Filing Separately (MFS). Despite this status sounding like someone’s dressing for divorce court, it can be useful in certain circumstances – or harmful.

Read More

Time for Year-End Tax Planning

This year is far from over for tax planning – for some moves, you have even longer – but now’s the time to start looking and acting on your tax tactics given your circumstances and the 2023 you’ve had so far. What you do or don’t do now could save or cost you next April.

Read More

The Latest on Proposals for a Wealth Tax

Should the rich pay more taxes? Are they dodging their equitable responsibility? Or do wealth taxes discourage people from the American dream of trying to get rich? Taxes are what the other guy in America should pay and the rich, with headline exemptions like Warren Buffet and Bill Gates , usually join the chorus of taxpayers who say they don’t want to pay more taxes no matter how much they’re worth. Call the concept one of a fair share or just simply unfair, a national wealth tax continues to ignite debate and legislation. What’s the latest?

Read More

Tax Planning for Gig Workers

The gig economy has opened moneymaking avenues for taxpayers who otherwise might have trouble making ends meet. But hustling has a price: Gig jobs also ignite tax complications that many of those workers probably don’t know about.

Learning about those obligations too late can cost gig workers back-tax penalties and interest. They can also result in those workers sabotaging their own tax situation and paying too much money to the government. What do gig workers need to know about their complicated tax situation?

Read More

Tax Considerations of Turning Your Hobby Into a Business

For many, owning a small business is the American dream. However, the tax situation incurred by turning your hobby into that business can be a real American headache. Still, who can resist the allure of a job that’s loved and makes the hours fly? You don’t have to resist it. Just be sure of what you’re getting into with Uncle Sam.

Read More

Tax and Financial Planning for Special Needs

The astronomical costs of a disability can extend beyond extra therapy and special equipment to, potentially, a lifetime of lost earnings.

There is some help. The federal government has tax deductions and credits connected with raising a child with special needs, for instance. And though historically a trust has been only financial avenue to care for a disabled loved one, another vehicle is gaining traction.

Many tax and financial moves in this area come down to one question that’s unique to this planning: Will money interfere with a disabled person’s ability to get indispensable government benefits?

Read More

Start Planning Now For Expiring Provisions of the TCJA

Time flies when you’re dealing with taxes. For instance, eight years must have seemed like an epoch when Washington passed the Tax Cuts and Jobs Act of 2017 (TCJA), the biggest federal tax reform in decades and one that altered tax brackets, deductions, and estate planning, to name just a few.

Best of all, lawmakers probably thought back then, we won’t have to worry about some of these provisions changing until all the way off in 2026!

Except suddenly, we now have less than 26 months to get ready for the end of nearly two dozen TCJA provisions that will happen without action from Congress. That’s barely enough time for some of the planning before what could be one of the biggest groundswell tax years of recent memory.

Read More

Small Biz Faces a Huge New Reporting Reg Next Year

Regulatory tsunamis come in batches. By now, for example, most of you have heard about the tax-reporting requirement slated to kick in next year, where the IRS would’ve learned about the income of individual taxpayers who made just $600 on the likes of eBay. That sounded like a looming nightmare — until the IRS suddenly put it off a year two days before Thanksgiving. (Sometimes removing tax regulations without warning creates as much confusion as adding them.)

Small businesses aren’t off the regulatory hook that easily for 2024. Come January 1, a new ownership-reporting requirement begins for millions of American companies. Now’s the time to prepare yourself and your company.

Read More

Should You File Your Client’s Taxes Early?

Common sense says that filing taxes as early as possible in the year gets an onerous chore off your plate and, chances are, gets your clients’ tax refund into their pockets quicker. Common sense can also be wrong if you need, as most taxpayers do, various tax-reporting forms that can arrive in early spring, if not later. There are also many other reasons you may, or may not want, to file your client’s taxes as early as possible.

Read More

IRS Again Postpones Tax Reporting of $600 Payments

The federal government is there to reduce taxpayer confusion.

That, at least, was one point of the reasoning for the recent IRS decision to again postpone a $600 tax-reporting threshold for people paid via third-party settlement networks. Those who made that amount on the likes of eBay and other online sales sites and who received payment via such platforms as PayPal and Venmo will not have that money reported to the IRS for another year.

Does this really let taxpayers off the hook? What strategies should you adapt for when the IRS does mandate this reporting?

Read More

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.

Read More

Electronic Commerce Creates Confusing Sales Tax Obligations

Any company engaged in e-commerce, i.e., selling online, knows that the ability to reach buyers and customers remotely can juice the bottom line. State and local tax jurisdictions around the country know that, too, especially the bottom line of their sales tax coffers.

Now every state with a statewide sales tax has a threshold past which remote sellers must collect and remit state sales tax. Failure to do so can incur big penalties, or worse, and there’s a lot to know based on where and what you sell online.

Read More

Death and Taxes: What Clients Should Know About the Death of a Spouse

Even your most financially savvy client isn’t going to think clearly after the death of their spouse. Taxes will be last on their minds. That’s where you’ll come in, nudging them toward tax and money moves both immediate and long-term, from filing returns to budgeting income to taking a step-up in basis. Above all, don’t assume grieving clients know these details or that they’ll remember them in one of life’s toughest moments.

Read More

CURRENT EDITION

Life Cycle of a Cost Segregation Study

The concept of cost segregation began in the 1960s, when taxpayers argued specific components of real estate had a shorter life than the depreciation tables allowed (39 years for commercial property and 27.5 years for residential real estate). After decades of legal cases, the IRS provided rules and safe harbors in 1996 and 2002. Taxpayers now can use cost segregation and remain compliant with IRS regulations. The real question now is: Does a cost segregation study really reduce a taxpayer’s liability? And if so, by how much?

Three Rules for the Augusta Rule

Today I want to talk about the quick question, “Can I rent my home to my business tax free?” The answer is not straightforward. It takes time to look at the specific set-up of that taxpayer’s business. It requires a bit of research. You need to know things like:
● What’s the fair market value of renting your home?
● How many days will you rent your home to your business?
● Can we substantiate that this rental is ordinary and necessary?

Amber Gray-Fenner already did an excellent job of explaining the Augusta Rule in an earlier issue of the newsletter. So, I won’t go over all the same points. I want to look at what the Augusta Rule is and how it came about. Then, we’ll look at three takeaways for you to remember in your practice and give to your clients.

Death and Taxes: What Clients Should Know About the Death of a Spouse

Even your most financially savvy client isn’t going to think clearly after the death of their spouse. Taxes will be last on their minds. That’s where you’ll come in, nudging them toward tax and money moves both immediate and long-term, from filing returns to budgeting income to taking a step-up in basis. Above all, don’t assume grieving clients know these details or that they’ll remember them in one of life’s toughest moments.

  • NOT A MEMBER YET?

    SUBSCRIBE TO GET ALL OF OUR
    GREAT ARTICLES AND RESOURCES!

  • Avoiding Passive Loss Limitations Through Short-term and Alternative Rentals

    Short-term rentals like AirBnb are becoming increasingly popular with taxpayers who invest in real estate. For many taxpayers, the appeal of these properties is the flexibility and cash flow potential. However, there may be an overlooked third tax benefit. In many situations these short-term rentals may not qualify as a rental activity to the IRS, and that may offer a big tax break. While many rental activities generate losses, this can leave taxpayers facing the frustrations of not always getting to deduct those losses right away due to the passive activity limitations.

    Read More

    How Business Owners Can Boost Income by Avoiding the $10,000 SALT Cap

    Taxpayers have been whipsawed by confusing rules for the $10,000 limit on deducting state and local taxes (SALT), the most politically charged piece of the Tax Cuts and Jobs Act (TCJA) of 2017. The cap has caused nearly 11 million individuals to lose an annual deduction worth $323 billion. But many owners of private businesses known as passthroughs can avert that financial pain. If you own your company and thus report your business income on your personal federal income tax return, here’s what you need to know.

    Read More

    GOFUNDME & KICKSTARTER: TAXABLE? DEDUCTIBLE?

    Millions of taxpayers in the United States are using crowdfunding websites like GoFundMe and Kickstarter to raise money for important needs, such as paying medical bills, paying legal fees, or funding a new business venture. Both the IRS and the courts have been surprisingly silent on the tax consequences of crowdfunding platforms. The good news is that established tax law provides a clear road map for answering most tax questions created by raising money from a crowdfunding website. By knowing these rules, taxpayers can use crowdfunding to raise cash and minimize their overall tax exposure.

    Read More

    My Client Stuck with a Mistaken C Corporation Election?

    My client formed three limited liability companies (LLCs) to hold his rental properties. Without consulting me, he filed Form 8832, Entity Classification Election, to elect C corporation treatment, effective January 1, 2020, for these LLCs. I want the LLCs to be disregarded entities, which is the most tax-efficient structure for his situation. What is the best way to undo these elections?

    Read More

    Quick Guide to Claiming Work-From-Home COVID-19 Expenses to Reduce Your Tax Bill

    This information is particularly important if you are the owner/shareholder of your own corporation – C or S corp. You can set up payroll and designate tax-free reimbursements for you to be working at home – as well other tax-free money for you and for your employees. (We will discuss employees momentarily. Yes, it’s essential.) If being an employee is your main source of income – watch out! The short answer to employees claiming an office in home deduction this year is... There is no deduction!

    Read More

    Five Tax Reduction Strategies for the Casual Cryptocurrency Owner

    With so many people looking for more ways to make money outside their 9 to 5 jobs, many are turning to money making methods using technology including trading in cryptocurrency. For tax purposes, the IRS considers cryptocurrencies property, not as currency. Just like other property types, stocks, investments, or real estate, when you sell, swap, or otherwise dispose of your cryptocurrency for more or less than you acquired it for, you incur a tax reporting obligation. As an example, there would be a $1,000 capital gain if 0.1 bitcoin is bought for $2,000 in June of 2020 and then sold for $3,000 two months later. This profit must be reported on the tax return and a certain amount of tax is due on the gain, depending on the tax bracket of the taxpayer. In this example, the gain would be short term requiring the profit to be taxed at the filer’s ordinary tax rate. These rates range anywhere from 0-37%.

    Read More

    Extra Taxes on S Corporation Distribution?

    My client plans to take about $15,000 in distributions in excess of his basis from his S corporation construction business. I know this generates tax for him. He’s in the 32 percent tax bracket and single. Does he also have to pay the 3.8 percent net investment income tax and the 0.9 percent additional Medicare tax on this amount? Is there a way for him to avoid taxes on this amount?

    Read More

    Reduce Taxable Income Up to $25,000 with Passive Rental Losses

    You have likely heard that owning rental real estate provides great tax benefits. This is true for a multitude of reasons, but there’s one benefit that is arguably the best of the bunch: The Small Taxpayer Allowance for Deducting Passive Rental Losses. Based on average household income levels, more than three-quarters of taxpayers can potentially qualify for this fantastic tax benefit that offers taxable income reduction of up to $25,000.

    Read More
    1 2 3 44
    Scroll to Top

    Thank you for subscribing to Tax Law Pro

    You are granted a non-exclusive, non-transferable, revocable license to access and use Tax Law Pro by Think Outside the Tax Box, Inc., strictly according to these terms of use.