It’s a voice message extravaganza as Joe and Big Al talk about tax gain harvesting on Dante in New York’s daughter’s custodial account, and the tax impacts of Leon in Chicago investing in his brokerage account. The fellas also spitball on whether Michelle in San Diego, en route to San Francisco, should buy or rent in her 60’s, the mega backdoor Roth and the pro rata rule for Sean and his cichlids in Winter Springs, Florida, and whether Jason in NOLA can do the backdoor after recharacterizing his contribution. Plus, should Kevin in Ohio make like the Steve Miller Band and "take the (pension) money and run"? Can Scott in Colorado make like Johnny Paycheck and "take his job and shove it" when it’s time for the rule of 55? And should Suzi and Peter consider long term care insurance and protecting their assets with an irrevocable trust? Access this week's free financial resources and the episode transcript in the podcast show notes at https://bit.ly/ymyw-464 Timestamps: 01:07 - Custodial Account Tax Gain Harvesting: Reported on My Daughter’s Taxes or Mine? (Dante, NY - voice) 05:17 - Tax Impacts of Investing in a Brokerage Account? (Leon, Chicago - voice) 10:50 - Three (okay, four) ways you make YMYW the show that it is Ask Joe & Big Al On Air for your Retirement Spitball Analysis 12:28 - Is it Better to Buy or Rent in My 60s? (Michelle, San Diego - voice) 19:50 - Mega Backdoor Roth & the Pro-Rata Rule (Sean, Winter Springs, FL - voice) 26:56 - Should I Take the (Pension) Money and Run? (Kevin, OH - voice) 32:13 - Money Makeover Guide - limited time special offer - download by this Friday! Complete Money Makeover - How to Do a Financial Facelift - YMYW TV 33:08 - Should We Consider Long Term Care Insurance and Protecting Our Assets with an Irrevocable Trust? (Suzi & Peter, San Diego) 39:23 - Can I Do a Backdoor Roth After a Re-characterization? (Jason, NOLA) 43:42 - Spitball My Early Retirement Plan & the Rule of 55 (Scott, CO) 52:29 - The Derails