So we've been struggling mightily to nail down where to go.  Of all the candidates we started with several months back we're now down to Puget Sound and southeast Florida.  We put together  pros and cons for each:

Florida

Pros
- Closer to J's parents and good advice on boat stuff
- Close to cruising grounds
- Nice live aboard winter weather
- Tons of boats
- No income tax
- Good cost-of-living

Cons
- Very hot and humid
- Boats are more beaten up
- Not excellent job market
- Hurricanes
- Possible bad cultural fit
- Work 10-7

Seattle

Pros
- Work 7-4
- Lots of boats
- Always wanted to spend time there
- Great job market
- Love the Pacific Northwest

Cons
- Would see less of J's parents
- Long voyage to just get to cruising grounds
- Cold winters for living aboard
- More expensive rent

We've hatched a scheme to reach a decision.  Stay tuned.