I have only lived on my boat for very short periods of time in Annapolis.(We were painting and remodeling my house so I moved aboard for about a month or so.) There are a lot of people who do live aboard around here and I count quite a few liveaboards as my friends. Depending on the marina, each marina seems to have a clear cut policy about live-aboards. Most welcome them but may have additional charges for power or restrictions. There are a lot of season liveaboards, either Snowbirds, or people who live elsewhere and use their boats as summer homes.
I found that I sailed a lot less during that period. I am not really sure why exactly because I did not have all of the complexity of getting underway that most long term liveaboards might have.
Winter is the hardest part. Some will accomodate live-aboards by moving them closer to the shore during winter. Most better marinas do have bubblers. Getting water in winter gets harder. Most marinas drain their dock water systems in winter. (I had a long hose and I ran it from a freezeproof spigot on the marina building once a week. Many of the local marinas have nice shower facilities which is what I used every morning. You are supposed to use your holding tank. If you do use your holding tank, it needs to be pretty large. I don''t know how you handle that in winter when you can''t leave the slip to get to a pump out. You need a reliable heater on the boat that can be run pretty much around the clock to keep things from freezing. I used a little electric space heater. That was probably a dumb idea but it worked. I had winterized every part of the boat that I was not using and would shut the seacocks whenever I was not actually using a particular piece of equipment. I was actually pretty lucky because the weather was unusually warm during the time I was on board.
Hopefully you will hear from someone who had lived aboard long term. Welcome to Annapolis and good luck with your plans.