Originally Posted by Sapperwhite
Also don't discount Westsail, you can pick one up for far less than 100k, and then put those savings into a few upgrades. Many of them are already fit out for offshore work (life raft, selfsteering, EPIRB, sea anchoring gear, etc. etc.).
The Westsail would do very nicely where you have a lot of wind, like the SF Bay area. All I know is they sail like an anvil around here (Chesapeake).