My old boss was a saltwater boat fan. He told me a lot of people buy a big boat and don't enjoy them as much as they expect to. They depreciate rapidly. But if you can get a storm knock a couple of holes in them you can get more money from insurance than you can selling them.
If you want a discounted boat. You can buy one of the totalled ones dirt cheap have it repaired and do some of the work yourself and get one for 20% of what it's insured value was.