Awww Ross, been there done that
I used to sail out of the northeast river and the Sassafras River to Turkey Point in August. We could count on NO WIND! We had a San Juan 21 with a 6 HP Chrysler outboard. The motor used to get floated and not start for 5 minutes. One time a big ship was heading right for use and there was NO WIND. That darn motor just didn't want to start. Darn thing started in the nick of time. I still have the motor but it hasn't be started in 20 years. First thing I did when the boat became mine was buy a new motor.I like the Chesapeake. You have a lot of nice places to sail to, ST Michaels, Annapolis, Baltimore, Still Pond. Great place to visit but I wouldn't want to keep a boat there.