I can tell you are hung up partially on the "adventure" part of the original boat. And if you pull it off it certainly will be an adventure to remember.
The US market is enticing becuase face it, there are just a heck of a lot of boats over there.
Unfortunately, like most of us, you are chained to a job for a while and that makes the logistics of a boat delivery
And as you note, we haven't even talked about solo sailing half-way round the marble...
I hate to say it but if you don't get hung up an a particualr type of boat (cat, tri, etc...) in 15-18 months there is usually a step aboard boat for sale
somewhere in Austral-Asia that would be an easy catch. Just be ready to pull the trigger.
A boat in the water
already doing it has the advantage that usually you can defer a lot of stuff on your list of repairs
and upgrades. i.e. the boat was doing it yesterday, why won't it presumably do it for a few more months while I take it home?
PS - I don't really troll the for sale
sites much. I do have a couple of saved searches on boats.com - Asia
mulit's and Asia
mono's 36-45' - and check them once in a while.