Jennifer Breton, Esq., Author at Think Outside the Tax Box

AUTHOR SPOTLIGHT

Jennifer Breton, Esq.

Jennifer Breton is an attorney with a focus on estates and trusts, business transactions, and tax.
Jennifer graduated with an LL.M. (Taxation) and an Estate Planning Certificate from Temple University Beasley School of Law. While at Temple, she won the LL.M. division of the prestigious American Bar Association Law Student Tax Challenge. Jennifer earned a J.D. from Widener University School of Law (where she notably served as the Editor-in-Chief for the Widener Law Review) and a B.A. in Political Science from West Chester University. Jennifer is licensed to practice in Pennsylvania, the United States Tax Court, and the United States Court of Appeals for the Third Circuit.

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Taking Care of Your Business: Estate Planning for Business Owners

You have put blood, sweat, and tears into your business and the hard work has finally paid off. Unfortunately, all the success may result in a significant tax bill for family members and very few resources available to pay it. Without an alternative, your business could end up on the chopping block for a fraction of what it is worth.

It doesn’t have to be that way! Careful estate planning can result in:
1. Minimization of estate taxes
2. Generation of needed liquidity to satisfy estate expenses

Continue reading to learn more!

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CURRENT EDITION

The Hidden Benefits of Private Placement Life Insurance (PPLI) for High-Net-Worth Families

For wealthy families, the world of finance can feel like a high-stakes chess game. With increasing state and federal income tax rates, new tax laws on the horizon, and the complexities of private investments like hedge funds, finding ways to grow and transfer wealth efficiently is more important than ever. Enter life insurance—a tool not just for its traditional role of providing death benefits but as a strategic ally in tax-efficient wealth management. In particular, Private Placement Life Insurance (PPLI) offers unique advantages that make it a worthy consideration for those with sophisticated financial needs and significant liquidity.

The Cryptocurrency Basis Day of Reckoning is Upon Us

Late on a Friday afternoon at the end of June 2024, the IRS dropped nearly 400 pages of new Digital Asset (née Cryptocurrency) Guidance. Most of it related to the forthcoming form 1099-DA. Along with the massive tome of terrible bedside reading, the service also published two new Notices and a Revenue Procedure. The Notices were about boring stuff, like temporary penalty abatement for backup withholding on digital asset transactions. This Revenue Procedure, however, will impact nearly every taxpayer that owned crypto prior to January 1, 2025. This procedure, RP 2024-28, has gone largely unnoticed thus far. On the surface, it seems like a godsend to taxpayers. Below the surface though, it is a ticking time bomb.

Reflecting On Syndicated Conservation Easements

In late June, IRS announced it would be mailing out a time-limited settlement offer that would allow taxpayers who are haunted by an investment in a syndicated conservation easement to settle. As I write this, the terms of the settlement have leaked. They strike me as overly generous. It does seem that the syndicated easement campaign of the IRS is coming to a close.

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  • 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.

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    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.

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    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.

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    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?

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    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!

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    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%.

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    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?

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    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.

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