Originally Posted by slax
2.) Continue to accumulate a nest-egg before leaving my current gig, while improving/sailing/learning my new home and honing the other skills needed.
3.) Work to support our (self/ship/dog) needs needs while abroad using IT/IS and ANY other skill-set I can tap into from my broad experience base in life, and use savings to ensure land needs are taken care of (support/family/etc...)
Slax - this is what I'm doing now. I have three years left for the nest egg. At which point I hope to buy and find a liveaboard marina in the southeast while I refit the things I want done.
Hopefully things don't change much in my life and that egg doesn't crack.
I'm also hopeful I can find IT work as a tester. I have 15 years of software testing experience and ought to be able to find contract gigs that will keep the kitty from draining too fast. Have you looked into sites that bid out jobs for contract IT work?
I've got a long standing relationship with a QA placement company in the U.S. west that I'm hoping will be able to funnel work my way when I'm parked for a fair amount of time.