I did an America Rail Pass a few months after retiring. I booked the first two legs (Syracuse to Chicago, Chicago to Santa Fe) one day in advance. Scheduled the next three legs (Santa Fe to Flagstaff, Flagstaff to LA, LA to SF)an hour before I left Santa Fe. Booked next three legs (SF to Denver, Denver to Chicago,Chicago to Syracuse) the day before leaving San Francisco.
No problems, but the Santa Fe station agent said I was traveling during a slow time.
Trains were nice. Staff was firm but friendly. Dining car breakfast and steaks were pretty good. The club car snacks are terrible and way overpriced.
The seats were comfortable to sleep one night in. They're like a large LazyBoy. Only had someone in the seat next to me overnight one leg so other nights I made a comfy nest out of both chairs. Two nights in a row sleeping like that was a bit much.
The Coast Starlight from LA to Oakland has some of the most stunning scenery I've ever seen.
Trains are often late. By a lot. Back in the 90s I took the family from DC to Orlando. 4 hours late. Coming back was over a 20 hours late!
Last trip Toledo to Syracuse left 8 hours late.