What happens if a storm wrecks your boat and you need cancer treatment? These are the things that retirement needs to account for imo. Everyone can live on wellfare and ramen indefinetly, but when the fecal matter hits the rotating air moving device id rather have the cash to stay alive a few more years.
Life is more complicated when have contract jobs or live on land, but if you retire on a boat, you simply move out of the way. If you have a couple days warning, hurricanes simply aren't big enough.
Boats are destroyed in hurricanes when the owner is freaking out about his house on land, or frankly, insurance scams. So some hull insurance won't pay out in tropical waters during hurricane season. So don't go there or get a different policy.
You can run into sudden squall issues, that is true.
One thing to think about is it might not be 10% cheaper it might be 75% cheaper. Even if you had to buy a completely new boat every decade because it sank (unlikely), it still might be cheaper than living on some land.
2) Health insurance (moderate to expensive, depending on my income and available subsidies). Or possibly seeking care in a country with a real (i.e universal) healthcare system. Cuba is in the Caribbean, and fairly accessible by boat.
You can't plan for every scenario; if I have terminal cancer I'd rather die surrounded by family and friends then exhaust my retirement in weeks or months to extend my life <1 year.
