I get the impression that you have figured out that finding a boat for living on and a boat for travelling on may be two different things. We had a young woman friend in New York who lived on an old Seafarer. The engine did not work and the sails looked like rags (not sure she really knew how to sail), but she had setup the boat for very comfortable living aboard.
As you say, there are lots of boats avaiable at very low prices so you can be choosing. If you want something that it is easier to singlehand, two things you will want are a reliable autopilot since you will need to be running around doing stuff and a good pilot makes this much easier and really good winches - self-tailing if at all possible, at least for the jib primaries, and oversized if possible to reduce the amount of power needed. Many manufacturers, particularly at the bottom end of the market, tended to put minimally-sized winches on to keep the sticker price down. Some people upsized them at purchase or later (perhaps when they wanted self-tailers to replace non self-taliers). Guess what I am saying is that there can be considerable differences between boats that are nominally the same.
Not sure that there are too many of them on the left coast, but a Nonsuch 30 Ultra (even a 26 Ultra) would be a good liveaboard. They are very beamy which makes them quite large for their LOA. The Classic model Nonsuchs are cheaper but you would have to decide if one of them would do the trick for you.
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.