Thanks for the response. Yeah I am in a similar situation- but besides looking for a lower rent option I just know I'd be much happier in the water. How bad are the winters in annapolis- have you had any trouble dealing with them? There don't seem to be a ton of liveaboards up on Lake Erie, I assume the cold might be the reason why.
I got a copy of the Nichols book and it is very helpful if a bit sobering.