I'm strongly considering buying either a 8-segment over 15 day, or a 12-segment over 30 day pass and taking the following route:
San Antonio to LA
LA to Chicago
Chicago to SF
SF to San Diego
San Diego to Seattle
Seattle to Chicago
Chicago to San Antonio.
If purchased ahead of time and with some careful planning I should be able to do all for $2,150-$2,350 (train expenses only).
I have several of questions I need help with.
1) What time of year would make for the best trip?
2) If I did this straight through but with only one night in a hotel per segment, would it drive me nuts? My main goal is to see the country and not the cities I'll be overnighting in as I've been to most all of them already.
3) I'm probably going to go it alone and will be getting a Roomette. Anything (other than the obvious) I should take with me to pass the time or better enjoy things?
4) Any other thing I should be mindful of before I go or in planning the trip?
Be sure if this trip happens you'll have to suffer through numerous YouTube videos! Thanks in advance all!