Ask HTM - Job Offer Conundrum, $55,000 Landing in Checking Account, & Teen Trading Tightrope #1210

In this Ask HTM episode, Joel and Matt answer five listener questions about real money decisions. They dig into whether taking a job with lower base pay but better upside potential makes sense, how to think about long-term disability insurance when a spouse's mobility is declining, and how to allocate a $55,000 lump-sum child support payment. They also weigh pre-tax contributions against a newly available Roth 401k and discuss how to introduce a teenager to investing, including whether a platform like Bloom is a good fit. The episode opens with a light debate over whether Joel is frugal or cheap for sending in his Darn Tough socks.