You did not clarify if you were going to do the work yourself or have the yard do it. For work to be done, Tidewater has a good reputation but there are many who also can provide excellent services but also have the better sailing grounds.
You may want to scout out quotes from Haven Harbour, Lankford Bay or Sailing Emporium in Rock Hall. The Western shore has so many options in
Annapolis that I will not list here but Jabin's comes to mind. Oxford Boatyard in Oxford is also a full service organization. If you can get a number of quotes to see who is the most economical, I would also ask if they will store you vessel at no charge while the work is done.
That can help you make the best choice as you move forward with this plan. It may take a weekend of driving down and visiting some of the yards and talking with the managers but that could be a fun trip.
Good luck with your plan. It sounds like a fun time.
Leslie
s/v Tango,
Cabo Rico 34
On the hard, Lankford Bay Marina
Chester River, MD