As per usual, our plans fell a bit short

we were heading up north for the summer to find somewhere to
work for a few months to refill the kitty for a little cruising after
hurricane season
but on the way north, we discovered our
keel joint was leeking and the
engine was suffering from MOLS or massive
oil loss syndrome -- soooooo we stopped in VA, hauled out and fixed the joint and
oil leak but we're behind schedule and a weeeee bit broke
so where do we go? We're 28 and 26 -- I've got plenty of IT
experience -- networking/infrastructure/servers/etc. but that's tough to find short term
employment in, pretty hand around
boats (engines, glass
work, etc. etc.) you learn a lot when you buy a
boat that was ignored for 20 years

and have worked in the hospitality industry before
girlfriend has worked in publishing and hospitality, is an artist and ideally would want to work for a
screen printer or something, but we're pretty flexible
I'm from South Carolina so the Chesapeake is one big empty spot in my knowledge of the US -- some people around the boatyard recommended either
annapolis or across the bay on the eastern shore -- Cambridge was mentioned specifically -- ideally we'd like to find somewhere we can live at
anchor or a
mooring ball and get around by bike or public transport and find jobs for a few months
any thoughts out there? Where should we check out? somewhere with a "downtown" however small would probably be preferable -- lots of businesses centered in a small area
should we go to Philly?
Annapolis? or are there some smaller cool areas that would great to live at
anchor in?