Woo-hoo!!!! Sounds like a fun tour--and a great plan to just do it instead of waiting!

I read one of the Crazyguy journals a few weeks ago from a man who rode across the US, part of the way with his 12 year old son and 16 (?) year old nephew, doing the trip in shorter legs so he wouldn't have to be away from home for too long. It seemed like a good approach to me, but he said that the logistics were difficult (either packing up the bike at the end of each leg and shipping it home, or finding a place in that location to store it until he came back) and it was disruptive--he'd just get into the touring groove and then that leg would be over. I think he was doing shorter legs of just a week to 10 days each, but it's something to keep in mind (of course one of the great things about your plan is that if you do a couple of two week tours and decide it's too disruptive, then you can change your plans for the next leg).

No ideas on the financing--I wonder how anyone ever does this (although I can't imagine that you're spending a lot of money if you're mostly camping and cooking for yourself--it wouldn't be any more expensive than being at home.).

Have fun with the planning!