If your working in Gaithersburg, will you be living nearby? (I Live in Gaithersburg/Rockville) If so, you should also consider marina on the Magothy River, Patapsco River/Rock Creek/Bodkin Creeks or even North of there.
The Chesapeake is one of the best cruising grounds in the world, you could spend your entire life sailing the bay and still not see it all. Yes, many places on the bay are shallow, but the majority is easily accessible and you will find wonderful anchorages abundant.
Marina prices vary widely, usually based on facilities and location. Annapolis is going to be the most expensive, but offer some great conveniences and of course a prime sailing culture, just be willing to pay big $$$ for it. The Magothy has few public marinas, I think the residence like that
But it is a ideal spot on the bay for sailing North or South. The Patapsco has many marina's and I am most familiar with them in Rock & Bodkin Creeks. I don't think you will have much of a problem finding a slip for a 34 foot boat anywhere, but it seems once you need 40' or larger the slips become more sparse around here, however the economic situation seems to have kept more boats on land than normal?
The one thing you will miss is the great restaurants in San Fransisco/Berkley.
Just a few quick thoughts, I'm sure others will chime in with their thoughts...