John P. Holloway, CPA, PC

06/16/2026

Planning to convert a rental into your primary home? Smart move — but beware: depreciation recapture (taxed up to 25%) and "nonqualified use" can still make part of your gain taxable, even after living there 2 years. Learn how to protect your equity and avoid surprises. Find out.

Learn how to navigate depreciation recapture and nonqualified use rules when converting a rental property into your primary home to maximize tax exclusions.

06/15/2026

Don’t let an outlived life policy drain your finances. Selling it can unlock cash—but may trigger IRS rules you don’t expect. Surprising fact: viatical settlements for the seriously ill can be tax‑free. Learn how to maximize proceeds and avoid tax surprises. Find out.

Learn the tax implications of selling a life insurance policy in a life settlement. Discover how the IRS taxes cash surrender value and capital gains.

06/15/2026

Surrendering, selling, or transferring a life insurance policy can lead to different tax implications. Watch this video for a brief overview.

06/12/2026

Think digital payments are invisible to the IRS? Think again. Surprising: Zelle won’t issue a 1099‑K — but income is still taxable. Avoid audits and surprise tax bills by organizing app payments and tracking fees/deductions. Find out simple steps to stay compliant.

Payment apps like Venmo, PayPal, Cash App, and Stripe can trigger tax reporting. Learn Form 1099-K rules and how to stay compliant.

06/11/2026

Youth sports can feel like a second mortgage — but some costs may be tax-savvy. Surprising: unreimbursed coaching costs and portions of day-camp fees can qualify as deductions or credits. Find out.

Learn about child care credits, charitable deductions, and NIL tax rules for youth sports. Expert advice from Midwest Tax Resolution in Carmel, Indiana.

06/10/2026

Turning side hustles into cash? Don’t let surprise tax bills wipe you out. Many creators don’t realize self‑employment tax kicks in at $400 and third‑party apps may not send 1099s. Learn what to save, track, and file to avoid penalties. Find out how.

Blindsided by a side hustle tax bill? Learn about the $400 self-employment threshold and how to stay compliant with Carmel-based Midwest Tax Resolution.

06/09/2026

Good news for tipped workers: a new below‑the‑line deduction (2025–2028) could reduce your federal tax by up to $25,000 — but beware: starting in 2026 the IRS will generally only accept tips shown on W‑2s/1099s. Want to make sure you don’t lose the benefit? Find out what counts and how to document it. Check it out.

Explore the final regulations for the new federal tip deduction. Learn about TTOC codes, $25,000 limits, and reporting requirements for 2026.

06/08/2026

Own a Qualified Opportunity Fund? The 2017 QOF tax deferral ends Dec 31, 2026 — which could create a "phantom" tax bill on your 2026 return. Don’t wait until it’s due. Learn smart moves (loss harvesting, charitable giving, deductions) to protect your liquidity. Find out how.

Capital gains deferred into Qualified Opportunity Funds will become taxable in 2026. Discover strategies to offset this liability and avoid IRS collection issues.

06/08/2026

Taxpayers with deferred capital gains in Qualified Opportunity Funds should prepare now for the potential tax liability due in 2026 and explore available tax-saving strategies.

06/05/2026

Working harder but one unexpected bill away from crisis? You’re not alone: 36% of Americans have more credit card debt than emergency savings. Learn simple steps to build breathing room, reduce financial stress, and protect your future. Find out.

Understand the growth of the emergency savings crisis and how to build financial resilience through cash flow visibility and debt management in Indiana.