Yup, very early days. So, doing a lot of reading and visiting various marinas, etc. Am looking at 35 foot liveaboard slip in Sausalito. It's on a private pier... not a yacht club... so, the cost, is reasonable. Of course, it doesn't have the amenities but that's fine by me.
Imho, my biggest challenge will be to find a boat that's seaworthy, that doesn't need emergency repair, so to speak. I don't mind working on a boat, learning how to repair stuff. In fact, I think it would be prudent to educate myself wrt that sort of thing. I just don't want to have to worry about the thing sinking in the middle of the night while I'm trying to sleep. And yeah, once I move to the next step, I'll hire a professional surveyor.
As for living on the hook? I may consider so later. However, at this point, I want to ensure I even like living on a boat, first. Hence, the slip for at least a year. For me, this is something I've long wanted to do. Figured I should at least try it out before arthritis, alzheimers, or all the other wonderful old-age stuff sets in! And hey, if it turns out that I hate it, at least I can say, "I tried!" ^_~