May 26, 2025

Listener Q&A: Trusts, IRMAA, Inheritance Taxes, Capital Gains, and More

Show Notes

In this special episode, we catch up on a backlog of insightful listener questions—covering everything from estate planning and Social Security taxation to Roth conversions and Medicare rules. If you’ve been wrestling with real-world retirement planning decisions, you’re not alone. Today’s episode delivers practical answers to the kinds of issues many people face but few have clearly explained.

We tackle:

IRMAA and Social Security Taxation – Does IRMAA include Social Security income if it’s not taxable?
Capital Gains on a Vacation Home – Should you delay estate planning until after the sale of a property? What about the "2 out of 5 years" exemption?
Paying Inheritance Taxes – If all your accounts list beneficiaries, how will state inheritance taxes (like Pennsylvania's) get paid on time?
Step-Up in Basis with TOD Deeds – In Oklahoma, does property with a Transfer on Death deed still receive a step-up in basis?
Impact of Home Sale on IRMAA and Roth Conversions – How does selling a vacation home affect your income-based Medicare premiums and Roth conversion strategies?
Medicare Enrollment Rules at Age 65 – Are you legally required to enroll in Medicare at 65 if not on a qualifying employer plan?
Trusts and Anonymity – How can you use estate planning tools while keeping your affairs private and self-directed?
Probate Friendliness by State – Which states make probate easy, and which ones almost demand a trust-based plan?
Inherited IRAs and Roth Conversions – Can a beneficiary convert inherited IRA funds into a Roth IRA for future tax-free growth?

If you’ve ever had a nuanced question about retirement or estate planning, chances are someone else has too—and we’re tackling them head-on in this packed Q&A episode.

Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.

📍Contact Devin’s team at https://carrolladvisory.co/podcast1

📍Contact John’s team at https://www.rossandshoalmire.com/

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now!

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517

Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

If you’re thinking "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We’re adding new content every week, and if you’re not following, there’s a good chance you’ll miss out. Follow now!

Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and look for the tab on the right side that says “Send A Voicemail.”

Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.

Contact Devin’s team at https://www.carrolladvisory.com/

Contact John’s team at https://www.rossandshoalmire.com/

Want to ask a question? You can find us in our Facebook group. https://www.facebook.com/groups/bigpictureretirement