Don and Tom explore one of retirement’s biggest emotional and financial questions: where should you actually live once work winds down? They discuss the hidden realities behind “low-tax” retirement states, including insurance costs, healthcare expenses, weather extremes, and the importance of family and community. The episode also features listener questions on retirement cash management, why annuities often create more problems than solutions, retirement savings strategies for LLC owners, and the ultra-wealthy “buy, borrow, die” strategy using securities-backed lines of credit.

0:05 Retirement dreams and deciding where to live
1:49 The myth of “low-tax” retirement states
3:18 Washington taxes, Jeff Bezos, and Wyoming winters
4:27 Florida’s hidden costs and brutal summers
6:04 Insurance shocks, pension taxes, and state tax surprises
8:04 Property taxes, sales taxes, and healthcare costs
10:12 Why family and community matter more than taxes
11:38 Florida thunderstorms and surviving the humidity
12:40 Comparing total living costs before relocating
13:52 Aging in place and the rising demand for one-story homes
15:34 Listener question: What to do with $192,000 sitting in checking
18:52 Why liquid savings may beat annuities near retirement
22:15 Delaying 401(k) withdrawals and retirement flexibility
24:47 LLC profits and retirement contribution limitations
28:06 “Buy, borrow, die” and securities-backed lines of credit
33:19 The risks of borrowing against investments
34:05 Free fiduciary advice versus commissioned sales pitches

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