Barney and Betty in Maryland hit the jackpot. How’s Barney’s strategy for net unrealized appreciation, retirement withdrawals, and asset location for his $5 million employee stock ownership plan? Nick in the PNW will have $8 million when he retires early at 53. Should he contribute to his 401(k) or do the good ol’ mega backdoor Roth until then? Those are just a couple of the fat wallets Joe Anderson, CFP® and Big Al Clopine, CPA spitball on, today on Your Money, Your Wealth® podcast number 470. Plus, should Allen in New Braunfels’ recently widowed sister contribute to her traditional IRA and do some Roth conversions? Should Alicia in Denver take Social Security early to pay off her rental property, and how can Vern in Wickenburg Arizona buy a new home before or during the sale of his current home? Finally, Bryan in Washington needs to know the best investment strategy for his thrift savings plan, and Lyse in Georgia wonders when in a market downturn you should start spending your cash. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-470 Timestamps: 01:06 - Retirement Spitball Analysis for My Widowed Sister (Allen, sunny New Braunfels, TX) 06:52 - $5M ESOP Strategy: Net Unrealized Appreciation, Retirement Withdrawals, and Tax Location (Barney & Betty, MD) 18:07 Why Asset Location Matters - free download Are You Ready to Retire? Review Your Retirement Readiness - YMYW TV 19:00 - Should I Take Social Security Early to Pay Off My Rental Property? (Alicia, Denver, CO) 23:22 - How to Buy a Home Before or During the Sale of My Existing Home? (Vern, Wickenburg, AZ) 26:50 - Should I Buy a Qualified Longevity Annuity Contract as a Long Term Care Insurance Alternative? (Ron, IL) 31:08 - I’ll Have $8M When I Retire at 53. Should I Contribute to 401(k) or Do the Mega Backdoor Roth Until Then? (Nick, PNW) 37:05 - EASIretirement.com - free retirement calculator 38:06 - What’s the Best Thrift Savings Plan Investment Strategy? (Bryan, WA) 40:21 - When in a Market Downturn Should You Start Spending Cash? (Lyse, GA) 46:00 - The Derails