Our Blog
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Why estate taxes aren’t the only inheritance-related costs to consider
- March 18, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
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Estate planning discussions often focus on the federal estate tax exemption, but most families face different challenges when transferring wealth. Probate fees, state-level taxes, capital gains exposure, and administrative complexity can all erode inheritances – even for estates well below the federal threshold. A comprehensive estate plan addresses these hidden costs, not just headline tax numbers.
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S-corporations 101: FAQs for business owners
- March 4, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
S-corporations are one of the most frequently discussed (but often misunderstood) tax structures for small business owners. While they can offer real savings on self-employment taxes, the benefits aren’t automatic – they depend on your income level, involvement in the business, and whether you’re ready to manage the added compliance responsibilities. Here’s what you need to know about how S-corps work, who they’re right for, and what’s required to maintain one.
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Healthcare costs for the self-employed in 2026: strategies for rising premiums
- February 18, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
With the expiration of expanded ACA subsidies in 2026, self-employed professionals are facing significant premium increases with no employer to share the burden. While healthcare costs are rising, strategic planning can help reduce your total cost. The key is treating healthcare like any other business expense – strategically, proactively, and with tax efficiency in mind.
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The mega backdoor Roth: a straightforward strategy for high earners locked out of Roth IRAs
- February 4, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
For high-income professionals locked out of traditional Roth contributions, mega Roth conversions offer a powerful alternative. By contributing after-tax dollars to fill unused space under the $72,000 annual 401(k) limit and immediately converting them to Roth, eligible savers can funnel tens of thousands annually into tax-free growth.
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Understanding Trump Accounts: what parents need to know about the new child-focused IRA
- January 29, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Trump Accounts are a new type of tax-advantaged retirement account for children, created under 2025 legislation and clarified by recent IRS guidance. While contributions can’t begin until mid-2026, families can begin preparing now. This article explains what is currently known, what remains uncertain, and how Trump Accounts compare to other common savings tools like Roth IRAs and 529 plans.
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IRS clarifies 100% first-year bonus depreciation rules
- January 27, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
The IRS recently issued new guidance clarifying how the permanent 100% bonus depreciation deduction will work moving forward. This allows businesses to fully deduct the cost of qualified property in the year it’s placed in service, rather than depreciating it over several years.
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Your 2026 tax season survival guide
- January 22, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
For most people, tax season brings a quiet panic about what they might be forgetting and a last-minute rush to pull everything together before the deadline. But it doesn’t have to be that way. With just a little preparation, you can avoid surprises, minimize your tax bill, and make the entire process smoother for both you and your advisor.
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How to use installment sales to spread real estate capital gains over time
- January 19, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Selling appreciated real estate? Learn how installment sales can help you spread capital gains over time, reduce your tax burden, and align payments with retirement or income planning goals. This guide explains how the strategy works, when it applies, and what tax rules to watch for, including depreciation recapture and related-party restrictions.
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Rental or business? Navigating the tax treatment of short-term rentals
- January 14, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Understand how the IRS taxes short-term rentals, from the 14-day rule to deductible expenses and 1099-K reporting. A must-read guide for short-term rental hosts.
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IRS grants employers penalty relief for 2025 tip and overtime reporting
- January 7, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
The IRS is offering penalty relief for 2025 as employers struggle to comply with new reporting requirements for tips and overtime pay under the OBBBA. While businesses won’t face penalties this year for failing to separately report qualified tips, overtime compensation, and occupation codes, this transition period is explicitly temporary—and smart employers will use it to prepare for full compliance in 2026.
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