...The woman who lets me live with her (the little woman), *an inlander (Minnesotan by birth (I'm only Minnesotan by marriage) ), has actually consented to considering a retire afloat scenario. *Don't know whether to start SE (like yourself), or something closer (SAN Juan's?) *Southbound sounds good after 23+ yrs in Alaska....
Can't tell you much about west coast cruising, although the San Juan's seemed like a great place the one time we were there. The southeast was as much an accident as anything - the boat was there when we bought her, and we had family in a few places in the region, so we just started there/
However, I can tell you that the west coast cruisers I met seemed to think we had it way too easy, with pretty good cruising routes between Maine/Nova Scotia and the Chesapeake, or between the Great Lakes and the Chesapeake, and almost entirely protected cruising routes etween the Chesapeake and the Florida Keys.
My impression (and that's all it is) is that the west coast cruisers tended to be somewhat more solitary, because they were often cruising long hauls between anchorages, and encountered others less frequently.
The southeast cruisers, on the other hand, seldom went more than 25 miles between good anchorages (even jumping off to the Bahamas means only a long day, not an overnight passage) , so we tend to see many of the same couples every few weeks. This tends to create a sense that you're among old friends, even when most of them are new acquaintenances or total strangers. The social life was as much or as little as we wanted; some cruisers hosted or went to happy hours every sundown. Others found those quiet isolated anchorages where all you would see were porpoises and pelicans, and no signs of civilization. Most of us went between the two extremes, more likely to party when a bunch are holding up for weather, and less likely when we were making distance (i.e., 40 miles - whew!).
Also, it is easy to follow good weather in the southeast.
Holding up in the southern Chesapeake for the end of hurricane season (if storms threaten or your insurance so mandates) keeps many that far north until early October, but from then on it is pretty easy to see where the average temperature was over 70 degrees - that's where the bulk of the cruisers were. While it did get cold on occasion along this route, you could probably count on one hand the number of times most of us had to dig out our pair of long pants between November and March or so.
So, if the Admiral is inexperienced and would feel uncomfortable about a 36 hour passage in blue water, and/or if you both would prefer a somewhat more social and relaxed lifestyle, then my impression is that the southeast might have more to offer.
Nice thing about cruisers - ask 2 of them for an opinion, and you'll get a dozen answers!