Feature Article Archives - Think Outside the Tax Box

Feature Article

By Joshua Youngblood

Freelancer Deductions: What You Might Be Missing and What You Need to Remember

Even savvy freelancers often miss deductions that could significantly reduce tax liability. The IRS offers legitimate ways for freelancers to deduct business-related costs, but it’s not always obvious which expenses qualify and which ones cross the line into nondeductible territory. This confusion is made worse when we see some of the terrible advice from so-called “experts” on social media. In this article, we’ll explore the most commonly missed deductions for freelancers, highlight real-world examples, and review what tax professionals need to keep in mind when advising these clients.

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Just How “Hot” Should IRC Section 751 Be?

Tax rules are generally designed with a purpose in mind. Most rules serve to define the tax base and tax rates. Many others serve a behavioral purpose to encourage or discourage certain activities. The focus of this article stems from tax rules that are a combination of favoring certain activity such as generation of capital gains, and a limitation on such gains for certain taxpayers, such as the so-called “hot assets” rule for partners under IRC Section 751, Unrealized Receivables and Inventory Items. While Section 751 has been in the tax law for decades, a new application of it was raised by both the IRS and California FTB. This article summarizes Rawat, TC Memo 2023-14, rev’d, No. 23-1142 (DC Cir., 2024), and FTB Legal Ruling 2022-02, and offers observations on their relevance to tax research and practice.

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The Ultimate Business Upgrade: Turning Your Partnership into an S Corp Without the Tax Bite

Looking to cut down on self-employment taxes on your partnership income? Converting your partnership into an S corporation might be the answer. If you currently run your business as a partnership or an LLC taxed as a partnership, you’re probably familiar with the sting of self-employment taxes. Unlike shareholder-employees of an S corporation, who only pay Social Security and Medicare taxes on their salaries, partners typically get hit with self-employment taxes on their entire share of the business’s net income. That can add up fast. By transitioning to an S corporation, you can restructure how you take your income—splitting it between salary and profit distributions. The big advantage? Those profit distributions are not subject to self-employment tax, potentially saving you thousands each year. So, if reducing your tax burden sounds appealing, let’s break down how a tax-free Section 351 incorporation works and what you need to know before making the move.

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Breaking Down Tax Benefits for Higher Education

With the rising cost of higher education and greater reliance on student loans, taxpayers are looking for every opportunity to ease the financial burden of earning a degree. Fortunately, several higher education tax benefits are available to help offset the high cost of tuition, student loans and other education-related expenses. However, certain eligibility requirements — such as income limits and tax filing status — often trip up taxpayers along the way. Understanding the nuances of these tax benefits for higher education can ensure your clients take full advantage of available tax savings.

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10 Ways Certified Tax Planners Can Prepare for Increased IRS Focus on Documentation During Audits

The IRS is ramping up scrutiny of high-net-worth individuals and businesses, increasing audit rates by over 50% for those earning above $10 million. Recent IRS initiatives backed by Inflation Reduction Act funding have intensified enforcement on wealthy taxpayers, large partnerships, real estate investors, and tech businesses. IRS agents are digging deeper during audits and expecting taxpayers to produce more documentation to support every position on their returns. To help clients navigate this environment, certified tax planners must take proactive steps to bolster documentation and audit readiness. Below are ten authoritative strategies, complete with industry examples, IRS policy references, and best practices, to prepare for the increased IRS focus on documentation.

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Renewable Energy Tax Credits: An Opportunity to Sustainably Optimize Taxes

Investment Tax Credits (“ITCs”) and Production Tax Credits (“PTCs”, and together with ITCs, “RETCs”) have existed for decades and reflect the U.S. government’s commitment to incentivizing clean energy solutions in industry and commerce. The availability of RETCs was most recently extended by the Inflation Reduction Act of 2022 (“IRA”), which fundamentally transformed policy in this space by tying such credits’ expiration to the U.S. reaching certain targets for greenhouse gas reductions. While the recent change in Executive Branch leadership casts doubt over the longevity of RETCs, a full repeal seems unlikely given the scope and scale of domestic projects which utilize and benefit from such credits. This article discusses how RETCs may benefit both buyers and sellers in an increasingly uncertain environment.

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Client Alert

Leaving the United States, Part III: Dual Citizenship

In Part I of this three-part series, we discussed the implications and taxes for American expatriates. In Part II we turned our attention to renouncing citizenship. Here in Part III, we will consider the halfway point of dual citizenship. And as you would expect, taxes are a serious consideration.

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Client Alert

Editor’s Pick: BOI Reporting: A Game of Legal Ping-Pong

For tax professionals trying to guide their clients on Beneficial Ownership Information (BOI) reporting, the last few months have felt like watching a never-ending game of legal ping-pong. Deadlines have been set, overturned, reinstated, delayed, and challenged in court—leaving many businesses (and their advisors) unsure of when, or if, they need to file.

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How to Advise on the EV Tax Credit

At one time, a federal tax credit toward the cost of an electric car seemed like a permanent idea to help fight pollution and climate change. Now, a political shift in the U.S. endangers the notion and, more to the point, makes advising clients tougher in a tighter timeframe. How and when can those clients interested in an electric car and the credit still secure a tax break?

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Client Alert
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