Tax Planning Strategies: EDU #2539

The Retirement and IRA Show

Jim Saulnier, CFP® & Chris Stein, CFP®

Business, Investing

4.3 • 729 Ratings

🗓️ 24 September 2025

⏱️ 79 minutes

🔗️ Recording | iTunes | RSS

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Summary

This week, with Jim away at a conference, Chris is joined by Jake for an EDU episode that takes the shape of a Q&A, focusing on tax planning strategies. The guys cover a series of emails that highlight how different tax rules and opportunities intersect with retirement planning, income management, and financial decisions.

(10:30), the first question explores how the new OBBB changes—particularly the $40,000 SALT deduction and $6,000 senior deduction—are affecting Roth conversion strategies. Chris and Jake break down who might benefit from larger conversions, who may want to scale back, and how the extension of lower tax brackets plays into long-term planning.

(26:45), a listener with high health care costs asks what qualifies for deduction, how the 7.5% AGI threshold works, and whether items like chiropractor visits and insurance premiums count. The guys walk through the rules, the limits, and which expenses can make a difference.

(39:00), the third question looks at the backdoor Roth. A “long-lost” 401(k) rolled into an IRA raises concerns about the pro rata rule and whether it threatens the clean execution of annual conversions. The guys explain how to handle the rollover and keep the strategy on track.

(49:45), tax-loss harvesting and the wash sale rule take center stage. The listener wants to know how dividend reinvestments across different accounts might complicate reporting and whether timing strategies can keep things clean. Chris and Jake lay out how the rule works and what to watch for.

(1:02:45), a self-employed listener asks if funding a solo 401(k) before converting to Roth could save self-employment tax. The guys explain the mechanics, the limits on employer contributions, and the modest but real savings this tactic may offer.

The post Tax Planning Strategies: EDU #2539 appeared first on The Retirement and IRA Show.

Transcript

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0:00.0	The retirement and IRA show represents the words and views of the show hosts exclusively and should not be construed as investment legal or tax advice. All information is believed to be from reliable sources. However, we make no representation as to its completeness or accuracy. All economic and performance information is historical in nature and is not indicative of any future results. Any indices mentioned on the show are unmanaged and cannot be invested indirectly. Diversification and asset allocation strategies do not assure profit or protect against loss.
0:23.8	Never make any investment or financial decisions based on information offered on this show
0:26.8	without first consulting your financial legal or tax advisor.
0:29.7	Financial planning services offered through Jim Solnior and Associates LLC, a registered investment advisor.
0:47.0	This is the retirement and IRA show coming to you from beautiful Northern Colorado.
0:52.7	Join us as certified financial planner Jim Solnier, as well as Colorado State University Finance instructor and certified Certified Financial Planner Chris Stein teach you about IRAs,
0:58.0	borrow-en-case, annuities, Social Security, pension plans, and estate planning in a fun and enjoyable show.
1:05.0	Whether you are listening live in Colorado or streaming from their website or iTunes podcast,
1:10.0	Jim and Chris want you to know that
1:12.3	they're available to help you plan for your retirement. Just visit their website at Jimhelps.com.
1:18.4	That's Jim H-E-L-P-S.com and click the Meet the Team button on the homepage. Now here's Jim and Chris
1:26.0	with today's show.
1:30.6	Well, hello and welcome to the Retirement and IRA show EDU edition for this week. It is technically an EDU show, but it's going to
1:37.2	feel a lot like a Q&A show. The reason for that is Jim is currently attending a conference and is unavailable today.
1:45.6	So we took today as an opportunity to invite Jake from the office back on.
1:52.3	He's been on the show quite a few times at this point.
1:55.3	And he and I are going to dig into a handful, maybe four or five tax-related questions, kind of leveraging Jake's
2:07.1	knowledge of taxes, since he is, among other things, an enrolled agent.
2:12.1	So spent extra time with learning the intricacies of the U.S. tax code.
2:19.4	So we're going to get caught up on a few tax-related emails that have come in from listeners.
2:24.7	So, again, while this is technically the EDU show for the week, it's going to be, for all intents and purposes, a Q&A show.
2:32.3	So Jake, thanks a lot for joining me today.
	...

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