Guest Article Archives - Page 6 of 47 - Think Outside the Tax Box
By Peter J Reilly CPA

Hobby Loss Regulations And Loper Bright

For me, the most exciting Tax Court opinion of 2025 was Judge Joseph Goeke's supplement to his 2024 opinion in the case of Gary M. Schwarz. With a $1,851,878 tax deficiency, it is the largest hobby loss opinion since 2019. (The really big dollar cases tend to settle.)

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Data-Driven Sales for Accountants: How to Use Analytics to Identify Sales Opportunities

As accountants, we are no longer just the stewards of our clients' books; we're their trusted advisors, guiding them to financial success, helping them optimize performance, and keeping them compliant with tax regulations. We use data analytics tools to guide and advise our clients to make informed decisions. However, we sometimes overlook using the same tools to advance our practices. We can leverage analytics tools to unlock new sales opportunities, offer enhanced services, and build deeper client relationships. Data-driven sales is a strategic approach to growing your practice consistently, boosting client satisfaction.

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Some Tips to Help Clients Make the Most of the New Tip Tax Deduction

The One Big Beautiful Bill Act relieves some of the tax burden that comes along with tip income for tax years 2025-2028. But not in some of the ways that it was initially explained. Yes, tip income is still taxable income. No, customers do not have to pay tips in cash for them to be deductible. But the tip does have to be voluntary, qualified, and reported to the IRS.

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Turning Extra Hours into Extra Cash: What You Need to Know about Overtime and the OBBBA

Do you love giving your clients great news? I do. Especially when it is about a tax benefit they can receive as the result of the hard work that they have put in throughout the tax year. That is what the overtime deduction is for the taxpayer. A little bit of tax relief for their hard work. But before sharing the good news with them, we need to make sure that we understand that No tax on overtime is not a blanket statement that will apply to all overtime compensation and all taxpayers. It is our responsibility to do our due diligence to understand who it will impact and how.

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Deducting Gambling Losses: Part 1 (OBBBA Updates)

The tax code is not kind to gamblers. All gambling wins are reportable as income. Losses are only deductible to the extent of wins and even that has limitations. Expenses of gambling, such as travel, meals, and lodging, are not deductible for casual gamblers. In Part 1of this two-part article we will discuss deducting gambling losses for recreational and professional gamblers. We will also discuss additional deductions professional gamblers can take and how they were affected by the OBBBA.

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TAX COURT ROUNDUP – August 2025

This month's Tax Court cases feature warnings to lawyers (and appraisers?) in the ongoing syndicated conservation easement wars; teasers about the impact of Loper Bright Ent. and Section 7701(o)(1); useful practice tips, and the conclusion of Boechler, P.C. (equitable tolling won't save a losing case).

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The Think Outside the Tax Box OBBBA Quick Reference Guide

The One Big Beautiful Bill Act (OBBBA) marks the most sweeping overhaul of the tax code since 2017, reshaping rules across personal and business income, education, healthcare, and credits. To help you stay ahead of the curve, Think Outside the Tax Box is proud to share our Quick Reference Guide, designed to keep you and your clients informed, prepared, and proactive.

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460(e) – Leveling the Playing Field for Construction

Buried in the middle of the One Big Beautiful Bill Act (OBBBA) is a small section with huge tax savings for multifamily developers – expansion of the 460(e) revenue recognition method exceptions. Previously only available to smaller construction contractors, the new law opens up a potential windfall for larger scale developers.

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Everything Old Is New Again: In Many Ways OB3A Is a Return To Obamacare 1.0

The good news is that none of the changes to the Affordable Care Act, Medicaid, or other health-insurance-related tax items in the One Big Beautiful Bill Act (OB3A) were retroactive to the beginning of 2025. The bad news is that the first set of changes is coming in 2026. The worse news is that some changes that were not included in the final version of OB3A are included in a new Federal Rule – but the provisions of the Federal Rule are only temporary. Basically, what we have is some federal rulemaking that was designed to give Congress time to codify the rule’s provisions into law, but only some of the provisions were codified – which simply means the provisions are merely temporary, not invalid. This article is going to discuss some of the important provisions concerning healthcare coverage that are included in OB3A, one that didn’t make it into the law, but that is in the new Federal Rule, and two that kind of blew up on social media but aren’t in OB3A or in the new rule.

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