The Annapolis pump-out boat won't service the North Anchorage unless you have the required permissions from the Naval Academy Superintendent; I called the Office of the Superintendent last year and no one knew how to issue permission. Annapolis won't serve boats on the Naval Academy moorings in Weems Creek either as you aren't supposed to be there.
The water taxi will serve the North and South anchorages during boat show (see my note above) and the Academy moorings in Weems Creek. There is plenty of room to anchor in Weems.
Prices go up for slips during boat show. I don't know what the status is now but most years things are tight by now.
The lesser known places are last to fill up. Try Annapolis Harbor Boatyard and all the other small places East of Annapolis City Marina (check ActiveCaptain.com).
City mooring balls are first come first served. You should be able to get a ball as late as the weekend before the show starts.
If you don't mind renting a car there is lots of room on South River and in Galesville. Note that parking at the show is a real pain.
It is worth noting that a lot of the work force for the shows are cruisers who show up a month ahead for prep. Moorings, slips, and anchorages fill up early.
when we lived there back in the late 80's, it was not unusual to get to town, at least a week or two before the boat show (set up is a week before the sailboat show), to get a slip or mooring, and most of those available were at private residences, yacht clubs and further out of town.
This late in the season you will likely have to find a spot well away from Annapolis, as most dockage will book up years in advance.
Hi, we are presently at Eastport Yacht Center in Eastport on Back Creek, I believe they have some slips available, plus we are leaving today Monday 10/6/14 and You should be fine in this slip, it is out front so it does get lots of boat traffic, and some waves from high winds, but not a bad place...clean facilities, and laundry, wifi, easy walk about 1 mile or so into the boat show, or can catch the water taxi at the docks. Davis pub is a short walk 1/4 mile and have great food, sandwiches, burgers, salads, wings, typical Bar food. Also a deli like bagel shop 1/8 mile, also has great breakfast item and coffee, its straight out 2nd street just up from marina, continue to the other end of 2nd street about a half mile to the Chart house, fine dining, and water taxi stop we used to ride over to chart house and walk back to marina because not as many water taxi's service back creek, but I am sure for the boat show they will have lots running. Good luck and enjoy the show, it's always a fun time.