All Articles - Think Outside the Tax Box

CURRENT EDITION

By Peter J Reilly CPA

Tax Tales I Let Slip in 2025: From Whistleblowers to Easement Woes and Beyond

One of my greatest frustrations as a tax writer is that I just don’t have the time to cover everything that I notice. Early in my blogging career, when I was younger and had more energy, I set myself on a Monday, Wednesday, Friday schedule like the college professors I envied. Even that did not keep up with everything I noticed, so periodically I would do a post that had short blurbs about interesting things I didn’t dig further on. Here is an example from 2010 of a post that covers an entity not considered a church by the IRS, S corp shareholder basis issues, definition of alimony and two Chief Counsel Advices on TEFRA issues. So here are some things for 2025, that I opened a file on but never managed to make an article with.

READ MORE

Vibe Preparing: Ignoring Partnership Agreement Impacts on K1s

Nothing derails a busy season schedule like being forwarded emails from client’s investors asking “are you sure the loss is allocated correctly?” It can expose a weakness in technical expertise – especially when it’s a partnership K1. Whether the operating agreement includes Safe Harbor or Target Capital allocations is one of the most important places to start for a preparer. And knowing these basics can be the difference between a confident reply or a lost week.

Read More

Deducting Gambling Losses: Part 2: Sessions Method

Recently I polled my peers on a social media platform dedicated to tax professionals. My hope was to find a resource for tax rules on a state level for handling gambling sessions. I knew it would be an uphill battle to get the information needed for a comprehensive guide state-by-state. What surprised me was the response. A large percentage of tax professionals were either unaware of gambling sessions or were unclear on how gambling sessions were handled in their state. Since gambling sessions might be the best way to reduce taxes on gambling wins, a lot of money might be left on the table with clients paying the price. Even if the state a tax professional prepares most tax returns for does not have gambling, the likelihood a client travels to a state that does, gambles, and wins is high.

Read More

TAX COURT ROUNDUP – September 2025

If reviewing Tax Court opinions teaches one thing, it's that tax legislation is too important to leave to legislators. Tax Court Judges are hyper-qualified; they need to be, to deal with what this month shows.

Read More

Charitable Impacts of the One Big Beautiful Bill Act

For charitable-minded taxpayers, several provisions in the One Big Beautiful Bill Act (OB3 Act) will impact the tax reduction associated with their charitable giving starting next year in 2026. In one case, the change increases the deductible amount, but all other changes surprisingly reduce the value of charitable contribution deductions. This article will review how the OB3 Act changed the charitable contribution deduction landscape and strategies for tax year 2025 and beyond to maximize the tax reduction value from charitable contributions.

Read More
Client Alert

A Tax Tailored for Twenty-Six: OBBBA’s Impact on College Endowments

Chapter 4 of the One Big Beautiful Bill (OBBBA) is titled “Investing In American Families, Communities.” Subchapter B of Chapter 4 is “Permanent investments in students and reforms to tax-exempt institutions.” That is where you will find “Modification of excise tax on investment income of certain private colleges and universities.” What is really amusing about this rewrite of IRC Section 4968 “Excise tax based on investment income of private colleges and universities” is that it applies to such a small number of institutions that you can identify them with a decent degree of certainty from publicly available information. The tax does not apply to state universities.

Read More

10 Key Things Tax Professionals Should Know About State and Local Business Incentives

State and local business tax incentives are powerful tools that can significantly reduce a company’s tax burden and influence business decisions. Every U.S. state offers some form of incentive to attract or retain businesses, from tax credits and exemptions to cash grants and property tax abatements. For experienced tax professionals, understanding these incentives is crucial for effective tax planning and helping clients maximize savings. Below are ten key things to know about state and local business incentives, along with real-world examples and actionable insights. We’ll also wrap up with essential dos and don’ts when advising clients on these programs.

Read More

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.

Read More

Big Beautiful Promises of No Tax On This, That, and The Other Thing

President Trump’s campaign promises oriented toward working stiffs and geezers – No Tax on Tips, No Tax on Overtime, No Tax on Car Loan Interest, No Tax on Social Security – were not precisely fulfilled in the Big Beautiful Bill, but they were not ignored. Rather than the exclusion implied by “No Tax,” we get deductions. Just so we don’t miss the connection, the first three get their own chapter in the Big Beautiful Bill – Delivering on Presidential Priorities to Provide New Middle-Class Tax Relief. The bone thrown to seniors is an exemption.

Read More
1 3 4 5 6 7 65
  • NOT A MEMBER YET?

    SUBSCRIBE TO GET ALL OF OUR
    GREAT ARTICLES AND RESOURCES!

  • Scroll to Top

    turn new laws into new opportunities download our FREE ebook

     

    Download Our FREE Magazine!

    Download Our FREE Magazine!

    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.