John P. Holloway, CPA, PC

09/02/2026

Should you pay off debt or invest first? The answer isn’t always what you’d expect—today’s higher interest rates, emergency savings, and tax factors can change the math. Learn how to balance debt payoff with smart investing for your long-term goals. Read now.

Should you prioritize debt payoff or investing? Learn how rising interest rates affect your mortgage, tax strategy, emergency fund, and retirement choices.

09/01/2026

Did you know an executor can become personally liable for unpaid estate taxes if the estate is handled incorrectly? Protect your finances while settling a loved one’s affairs by knowing the key IRS forms and steps that can help. Read now to find out how to avoid costly mistakes.

Learn when an executor can be held personally liable for a decedent's taxes and how to protect yourself using key IRS procedures and filings.

08/31/2026

Planning for the future isn’t just smart—it’s essential. A strong succession plan can help protect your business, reduce disruption, and keep operations running smoothly if the unexpected happens. Learn how proactive planning can safeguard your legacy and next chapter. Read now.

Learn the importance of succession planning to protect business continuity and ensure a smooth leadership transition. Contact Midwest Tax Resolution for advice.

08/31/2026

Succession planning helps ensure a smooth transition, protects business continuity, and reduces disruption when key people leave or pass away.

08/28/2026

Got a NYC second home or investment property? A new pied-à-terre tax notice doesn’t always mean you owe—many owners are being flagged in error. Learn what the notice means, what documents can help protect you, and why quick action matters. Read now.

New York City is mailing preliminary pied-à-terre tax notices. Discover what actions you must take if you receive a letter to protect your high-value property.

08/27/2026

September 15 is the Q3 estimated tax deadline—and missing it could mean surprise penalties later. If you earn income without enough withholding, this quick guide explains who needs to pay, how to avoid underpayment issues, and how online payments can make it easier. Read now to stay ahead of the IRS.

The third 2026 estimated tax payment is due September 15. Learn who should pay, safe harbor rules, penalties, and how to avoid a surprise tax bill.

08/26/2026

Your 50s can be the most powerful decade for retirement planning—and the choices you make now can shape your taxes, savings, and income for years to come. From catch-up contributions to Roth conversions, there’s more strategy involved than most people realize. Read now to see what smart planning can do for your future.

Maximize your retirement savings and lower your lifetime taxes. Learn how to strategically plan your retirement transition at ages 50, 55, and 60.

08/25/2026

Donating long-term appreciated stock can be a smart way to support charity and reduce taxes at the same time—often letting you avoid capital gains tax while giving more to the cause you care about. Curious how it works? Check it out.

Maximize your deduction and avoid capital gains taxes by donating long-term appreciated stock. Learn how with Midwest Tax Resolution.

08/24/2026

An HSA can help you save for healthcare expenses while offering valuable tax benefits. Learn who qualifies and how these accounts work.

08/24/2026

Did you know an HSA can offer triple tax advantages—before, during, and after your healthcare spending? If you’re enrolled in a high-deductible health plan, this smart savings tool could help you manage medical costs more efficiently. Read now to see how it works!

Learn how a Health Savings Account (HSA) works, including the tax benefits for contributions, growth, and withdrawals with a high-deductible plan.