Should Carl Spackler stick with his backdoor Roth strategy, or go for lower fees? Should Kevin go all Roth, or stick with his current three tax-diversified buckets strategy? (That depends - would he rather have $7 million tax-free, or $10 million in tax-deferred retirement accounts?) Can Lily claim all the extra allowances she can, to jam as much money as possible into her Roth? Can Dave retire now and ride his motorcycle into the Bavarian Alpine sunset, and does Peggy Lee need to be feverish about the tax underpayment penalty with her Roth strategy? Timestamps: 00:53 - Do I Need to Worry About a Tax Underpayment Penalty with My Roth Strategy? (Peggy Lee, North Dakota) 07:17 - What Am I Doing Wrong? Can I Retire Now? What About Taxes? (Dave, Germany) 15:28 - Back Door Roth vs. Lower Fees: Which Would You Choose? (Carl Spackler, FL) 21:40 - Should We Go All Roth or Three Tax-Diversified Buckets? (Kevin, NJ ) 28:53 - Can I Claim Extra Allowances to Contribute More to Roth IRA? (Lily, San Diego) 33:46 - Should I Split Money Between Multiple Brokerage Firms to Avoid Hacking? (Wesley from Unincorporated Gwinnett County, GA) 40:18 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-439 Register for the Q3 Financial Market Outlook live webinar, July 26, 2023, 12pm PT / 3pm ET The Ultimate Guide to Roth IRAs YMYW in US News and World Report's Best Personal Finance Podcasts to Listen to in 2023 Episode Transcript Big Al's Island Studio (photo) Ask Joe & Big Al On Air for your Retirement Spitball Analysis