"As I am about to be unemployed, I'm a little more interested in how or if it can be done with virtually nothing in the kitty..."
I am building a 22 ft trimaran. I've been laid off for years. We went to Oahu this winter. I looked about the marina in Waikiki and got the bug again. Anyway I am collecting what I need and will start building next month. I figure it might take me a year; hopefully sooner. I plan to go down the Mississippi (yes I am in Iowa) and down to the Keys my first voyage. One can also go up the Miss and out the SLS to NewFoundland; so that will be my second voyage perhaps. Anyway dream on.
I figure the boat will end up costing me about 30,000. I've scrimped and saved and got lucky and have enough money to do this. We will see. Being a surfer helps. I grew up on the ocean and really miss it. My wife is wondering I suppose. My son is highly interested, my daughter is not.
Great thing about the trimaran is it has a clearance of 12 inches with the skeg up, and it is trailerable as it folds. I have been looking at several designs and the Farrier22 seems hot. Only displaces 1500.
Being a graphic artist helps as work comes and goes and I can go most of it virtually. We will see how that works on a sailboat.!! Must have good internet connection; must have energy. Plan on wind and flexible solar panels. Read in this site about using driftwood for firewood. What a great idea!
I am used to living on minimal. So this will be interesting.
I wish you well taking off. I think a lot of Americans are thinking the same way. I have a feeling it is going to be very very difficult in the continent soon. Best to find an island and relax. Get away from this uptight trip. Or at least have that option. Get yourself back to reality. I don't know much that isn't real about the sea, the sun and the wind! And fishing; that's a dream.