Re: Complete Newbie...No Idea What I'm Doing...
Owning a sailboat automatically qualifies us all as insane, so you're okay there. Welcome to Nutjobs Anonymous. Living on a boat takes no skills at all, except perhaps a tidy approach to housekeeping and reasonable balance. Thing is, most liveaboards don't sail much. Who wants to sail their house?
So you won't likely learn to sail on a houseboat. You can, but it is work. And any boat large enuf to live on & heavy enuf to take offshore is gonna be less than ideal to teach you sailing. You can do it, but you'll need serious commitment and possibly an experienced mentor.
Love the attitude & goals. Here's a few possible routes to your dream:
1) Live in a tiny apartment (good practice!); work like the devil for two years. Sail in the evenings. Either buy a dinghy or small keelboat, or join a sailing club, where you can try out a bunch of different boats & get free lessons. When you are ready to live aboard cruise, you'll know sailing like only seat-of-the-pants dinghys can teach it, and you'll have some idea what you want in a boat.
2) Buy your big liveaboard cruiser; buy a sailing dinghy or windsurfer you can practise on. Or jump rides on other peoples' boats (OPBs). Again, combined experience & tutoring.
3) Get a beat up coastal cruiser cheap. Force yourself to keep it in sailing trim and to sail it often. If you are sure it is the one, start converting it for voyaging one system at a time, as money permits. This is a possible route, and the discipline you learn will set you up for voyaging. But it's a loooong route, figure 4-5 years at least, and you will be broke most of the time -- as every spare nickle goes into boat upgrades.
As for boats in that price range.... Yeah, they are around. Look into the following brands: Coronado, Cal, Ranger, C&C, Contest/Conyplex, Ingrid, Islander. All will need substantial effort before casting off -- make sure your candidates are at least in sound, sailable condition. Superficial neglect is okay, tho it sometimes hints at deeper problems. Solid engine is important. Don't rule out an Atomic 4 gasoline engine, if it is running well. Many older boats in your price range will have them. Some of these boats will sail well but bounce around & be small inside (Ranger, C&C); others will be roomy & secure in a blow, but not perform so good, esp. in light or contrary winds (Contest, Ingrid, Coronado).
Albin Ballad 30, Fionn