Your biggest obstacle in fulfilling your wish list here is finding a marina with a pool and one with reasonable cost. Can't think of one in Annapolis
area that fits that bill. There are a couple with pools on Back Creek in Annapolis, but they're all pricey. Mears, for example, charges $3.50 per foot per night. Nice facilities, but hardly worth the price
Herrington Harbor South off of Herring Bay has a pool. But not much in the way of other services.
West River Yacht Harbor in Galesville has a pool. It's a condo marina and usually has slips available from slip owners. There's also good services down the road at Hartges Marina. There's also a canvas
guy in town that is supposed to be OK.
Best bet could be Solomons. Spring Cove Marina has a nice pool and the place is kid friendly. There's also a lot of good services in Solomons.