Re: looking for marina
I know you say your not a yacht Club kinda guy but I would suggest checking out Maryland Yacht Club. Several live a boards there. I have been a member there for a year and just renewed. Great group of sailors there. Your commute to Columbia would be about 30 minutes depending. There plenty of shopping and marine stores around and you're not paying premium prices for Annapolis zip codes.
It can't hurt to look, nearby is Oak Harbor marina, they also have some live aboards. Well protected and great family owned place.
Good luck, if you want more info about either feel free to send me a pm.