Ask HTM - Side Hustles for Your Stocks, Capital Gains Harvesting, & Maxxing HSA Benefits #1213

A listener-question episode covering five money problems sent in by the audience. The hosts work through whether to opt in to a broker's fully paid lending program, whether a CPA's claim about taking $40,000 of capital gains tax-free holds up, and whether it's worth giving up state-provided health coverage to max out a spouse's HSA. They also take on the best formula or app for eliminating debt and whether catch-up contributions should be made with pre-tax or post-tax dollars. The show opens with a debate over whether mailing in a pair of Darn Tough socks makes Joel frugal or just cheap.