Re: Best U.S. city for sailing, living aboard, working
Actually, I think it's pretty easy to look at a map and guess. Great cruising grounds come from the most fractal landscapes because those create the most tiny nooks and crannies to explore. Those don't exist in many places in the US. On the west coast you get WA and BC from the Salish Sea. On the east coast you get Maine and nearby parts of Canada, the Chesapeake, maybe FL (though destinations seem minimal in comparison) and that is about it. Then there is Alaska.
Out of all of these locations only the Cheasapeake and Salish Sea have major cities, which may or may not be helpful for your particular career.
The Salish Sea is the only one of those two where year round sailing and cruising is commonly practiced.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior