Let's review the situation:  We have decent earning capacity, but virtually no savings.  I mean we have a non-negligible amount in 401ks but nothing liquid.  We have a slightly neglected house in a gorgeous location.  We have probably zero equity in this housing market.  I don't think we're underwater, but we might be.    On the other hand, 2 of our neighbors sold this summer for reasonable money.  So who knows. We could break even after paying off the realtor.  Hopefully.  OK, great.  Then what?

I think the sequence of events is this, roughly:

  1. Between now and next spring, liquidate a lot of junk and put in a lot of sweat-equity (but not money) on aesthetic repairs.
  2. List and sell, May through August.  Try for a profit, but be prepared to just break even.
  3. Move to month-to-month lease locally.
  4. Choose somewhere with lots of boats and jobs to job hunt.  Probably Miami, since it also provides easy jumping off to island hopping.
  5. Get a job there.
  6. Move to a month to month there.
  7. Boat-hunting.  Slowly and patiently.
  8. Choose and buy boat.
  9. Move aboard, pay it off, fix it up, learn maintenance and repair of marine diesel, electrical and electronic systems, hulls and decks, sails, rigging, etc..
  10. Save a cruising kitty.
  11. Quit, and head for the Bahamas and Caribbean.
  12. Work out the kinks for 6-12 months.
  13. Panama
  14. Passage-making
  15. Sustain on ~20K/year by eating a lot of fish, stopping to work in boatyards and on 3-6 month programming contracts, doing charters, maybe selling some photos and articles, and hopefully some deliveries.  
So that's the "plan" for now.  Let's see how it goes.

I found some cool pages on the theory and physics of sailing:

I want to start to get really specific with boat knowledge.  J measurements, cringle radii, clew vangs, fliberty-gibbet ratios, the whole bit. So I'm going to work on that.