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I have a pretty secure job, and my wife and I have, surprisingly, ended up financially solid at this point in our lives--50-ish. So, if anything, we are freer to tour and do whatever. As a community college teacher with tenure, I've pretty much got it made so long as I don't beat any students with a rock--and sometimes I'm tempted! And, to be honest in this discussion, MOST Americans--by a very wide margin--are employed and doing ok. It's just that we have a larger percentage of unemployed and underemployed than we've had in a long time. Keep in mind that the news agencies/media have a keen motivation to tell us all is in ruins: It sells.
If you are talking about the official TransAm route - the Rockies will be the least of your worries, Yellowstone gets winter very early. I would definitely plan on routing south, not staying on the TransAm or even the Western Express unless you are going very fast and will be done by mid-October. Sorry I can't actually propose a route for you.
Putting your fate in the hands of the conductor is always a gamble I suppose, but if they are reasonable it could be possible. Plus it will be dark - perhaps more sympathy invoked.
A Philadelphia-Hoboken bicycle route seems very tricky but I guess it could be done with careful planning. Sounds interesting.
- Riding the Western Express to Pueblo, CO (just to ensure myself that I can climb 5,000 feet and scale an 11,000 foot pass )