Re: Questions of living and travelling under sail..
33 OI is a good boat. In fact, that is what I'd get next if I wasn't wanting to build a bigger boat.
33 is small enough to sail by yourself and not big enough to cost a fortune (or at least a bigger fortune) in upkeep.
With her 3'10 draft, you can take her in shallow water but she can do blue water sailing too.
Do not expect to save any money living on a boat. It'll cost more'n living ashore.