I gotta point this out, though you may have thought of it.
Why not partner up on a boat? for the same price as a used 'project' boat ($15k =/-) you get a brand NEW boat and forever get to share the expenses. Scheduling is remarkably easy as you NEVER have as much time to sail as you think and if you both want to sail the same race occasionally, it's a 3 man boat.
You get to sail versus do a repair project.
I'm putting together guys in the Bay Area that are living on a budget but still looking to sail.
Consider the possibilities !!