Re: Best U.S. city for sailing, living aboard, working
Part of it has to do with what you want to do for a living, and part has to do with what kind of weather you like. I don't think I could survive the Florida summers, and don't really mind the upstate New York winters, but it does bring it's own live aboard challenges. If you want to be on the East Coast I think it would be tough to beat the Chesapeake as far as work/sailing balance. On the West Coast you have basically your choice of three areas, San Diego, San Fran, or PNW depending on your weather choice. If you are interested in the Hotel Restaurant business then that opens up some areas like North Carolina/South Carolina, Gulf Coast and Florida. New York/Boston/RI/Portland Maine all have there advantages as well if you like colder winters and more employment opportunities.
My ideal place would be Hawaii, but from my understanding the live aboard is hard to do there. I have family there and will likely end up there eventually.