John P. Holloway, CPA, PC

09/08/2026

Did you know your retirement savings may soon help cover long-term care insurance premiums without the usual 10% early-withdrawal penalty? Learn how SECURE 2.0 could make this important coverage more affordable and tax-smart. Read now to see what’s changing and whether you may benefit.

Learn how the SECURE 2.0 rule allows tax-exempt penalty distributions from retirement accounts to pay long-term care premiums starting after December 29, 2025.

09/08/2026

September 15 is the 3rd estimated tax deadline—miss it, and you could face underpayment issues later. If you earn income without automatic withholding, this quick reminder can help you stay compliant and avoid surprise tax trouble. Find out what to pay and why it matters.

The third installment for estimated taxes is due September 15. Ensure your self-employment or investment income is covered to avoid underpayment issues.

09/08/2026

If you rely on estimated tax payments, it’s important to make this installment on time to help avoid underpayment issues later in the year.

09/04/2026

Becoming the “family CFO” can happen fast—especially when you’re supporting kids, aging parents, and your own future at the same time. The surprising part? One money move can impact all three generations. Learn how to protect your retirement while helping your family. Read now.

Learn how to manage multigenerational financial decisions as the family CFO while protecting your own retirement savings and tax planning.

09/03/2026

Think your business travel or mileage deduction is safe with just a credit card statement? Think again. A recent Tax Court case shows how weak records can erase deductions and trigger penalties. Learn what documentation the IRS really expects—and how to protect your write-offs. Read now.

Protect your business deductions. See what the IRS requires for travel, meals, and vehicle mileage logs—and how to avoid 20% accuracy penalties.

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.