Pop my bubble: Buy a sailboat in Thailand and sell it in Annapolis for world cruising on the cheap

Posted by CandleTiger@reddit | sailing | View on Reddit | 118 comments

So I have this daydream I have been building up, and I need somebody with experience to tell my why it's hopeless and will never work. I'll be retiring in the next few years, and my budget extends to a nice boat OR a nice house but not both. The wife declines to spend retirement living on a boat and touring the world, so I'm thinking to do a temporary stint:

Am I crazy, is this a stupid idea?

Assumptions I'm making: