Roth Conversions: When to Make 'Em, When to Take 'Em

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A YMYW listener from MO and his wife are retired with less than $2M. Should they continue converting retirement savings to Roth for tax-free gains? What should they do about long-term care insurance? More importantly, is our listener’s name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, must “Peggy Hill” wait five years to withdraw her conversion or only its earnings? That’s today on Your Money, Your Wealth® podcast number 547 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, is Skipper’s retirement payout plan the killer deal he thinks it is? How can Jeff in Dallas pay less capital gains tax on his $3M single stocks, $1M 401(k), and potential eBay income? Is selling on eBay still a thing? Does Dolly in TN need to empty her inherited IRA within the next 10 years due to the SECURE Act? And how should Larry in RI navigate switching from his current employer’s health savings account to his future employer’s health reimbursement arrangement?

00:00 - Intro: This Week on the YMYW Podcast
01:11 - Should We Continue Roth Conversions in Retirement? What About Long-Term Care? (Cousy, MO)
13:03 - Must I Wait 5 Years to Withdraw My Roth Conversion, Or Only Its Earnings? ("Peggy Hill", MN)
21:50 - Is My Retirement Plan Payout the Killer Deal I Think It Is? (Skipper)
28:07 - How to Minimize Capital Gains Tax? (Jeff, Dallas, TX)
33:37 - Must I Empty My Inherited IRA Within 10 Years With The SECURE Act? (Dolly, Bristol, TN)
37:50 - HSA vs. HRA (Larry, RI)
40:48 - Outro: Next Week on the YMYW Podcast

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• Intended for educational purposes only and are not intended as individualized advice or a guarantee that you will achieve a desired result. Before implementing any strategies discussed you should consult your tax and financial advisors.
CFP® - The CERTIFIED FINANCIAL PLANNER® certification is by the CFP Board of Standards, Inc. To attain the right to use the CFP® mark, an individual must satisfactorily fulfill education, experience and ethics requirements as well as pass a comprehensive exam. 30 hours of continuing education is required every 2 years to maintain the certification.
AIF® - Accredited Investment Fiduciary designation is administered by the Center for Fiduciary Studies fi360. To receive the AIF Designation, an individual must meet prerequisite criteria, complete a training program, and pass a comprehensive examination. Six hours of continuing education is required annually to maintain the designation.
CPA – Certified Public Accountant is a license set by the American Institute of Certified Public Accountants and administered by the National Association of State Boards of Accountancy. Eligibility to sit for the Uniform CPA Exam is determined by individual State Boards of Accountancy. Typically, the requirement is a U.S. bachelor’s degree which includes a minimum number of qualifying credit hours in accounting and business administration with an additional one-year study. All CPA candidates must pass the Uniform CPA Examination to qualify for a CPA certificate and license (i.e., permit to practice) to practice public accounting. CPAs are required to take continuing education courses to renew their license, and most states require CPAs to complete an ethics course during every renewal period.

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