I can relate to everything but I am more of the motivated, skilled, etc. who is not in as much shape as you. However, now that the kids are mid-teens, once I get my youngest off to college, I will be embarking on the southern tier route from Key West to complete my perimeter tour then do several others. Look me up in a few years!
That is an excellent choice for a transcon. I have done it a number of times myself. In order for me to close the perimeter I would have to go from Bar Harbor, Ellsworth actually, to Fargo or to Minneapolis or thereabouts; not that I think closing the perimeter is any big deal. After all, I have done the atlantic coast three times, the ST a number of times, the PCBR, 2600 miles of the NT, and a lot more besides.
I was gearing up to do the ST this past winter, December-January, when a job I had been looking into did open up. I wanted to do the ST, but not being rich, and being in need of an income, the wiser decision was to take the job. Before then it was not clear whether or not the job would open, but it finally did. I don't know when I will be getting away on another long cycling tour. I have two daughters in Florida who are eight and seven. I send them money every month, and that requires a steady income. Maybe this summer I can do a round trip from where I live to Key West and back, but that would be about it for these days.