I just completed the first 4 segments on my rail pass!
1: Home->Chicago (1 overnight)
2: Chicago->Dearborn MI
3: Dearborn MI->Chicago
4: Chicago->Home (1 overnight)
I really enjoyed it! I'm the kind of person who loves watching the world go by, so it worked for me.
Biggest complaint - every train was in the ballpark of 2 hours late. It wasn't a big deal because I was expecting it, but it put me walking to my hotels after midnight which didn't cause any issues, but wasn't ideal. I had assumed that at least one segment would be close to on time, but no. I was surprised by the number of people complaining about "why is the train stopped". I knew the train would randomly stop for rail traffic and whatnot. The best was whoever was doing the announcements on the Wolverine coming back from Dearborn - they announced that we were stopped because of a car on the tracks, and continued with some "real talk" about how we need to stop doing that - it was hilarious. He was calm, but obviously frustrated, as I take it this is a common occurrence - the previous day we took on passengers from an earlier train that was taken out of service, and I read that they had possibly hit a vehicle.
Slight complaint - announcements are hit-and-miss. In general, the calling out of stations and how long we'd be at each was excellent. Some conductors were better at announcing reasons for (or simply acknowledging) stops and delays. On my outbound trip, the conductor did a great job of pointing out points of interest along the way. I'm pretty sure he even pointed out a moose sighting! On the way back, no "sightseeing" announcements at all.
I was able to sleep on the train. Not well, but not too bad, either. Both nights I had both seats to myself. Leaving Chicago the train was understandably full, but it cleared out before night, and I was able to snag a seat alone when I wanted to go to bed. I don't think I'd be able to sleep if someone was sitting next to me, as that would limit my motion a lot. I'm a little worried about not having both seats to myself on future trips.
1 night on the train was fine, 2 would be iffy.
I got off at every fresh air break to walk a few steps (formerly called smoke breaks, I assume). Since every train was running late, these stops were mostly 3-5 minutes, not enough time to do much (like look for fresh food).
I spent most of my time in the observation car, though that was a little silly at times because the coach seats are more comfortable. The attendant gave away my seat as we approached Chicago because I was spending so much time in the observation car. I went back to my seat, and someone was in it - even though my coat had been in the seat. ?? So that was annoying, but ultimately not a big deal, other than me having a confrontation with the woman asking why she was in my seat (and she very definitely was not moving, lol).
Food was okay. I ate 1 dinner in the dining car to see what it was like - it wasn't bad, but definitely not worth the $45. Next time I might try lunch, just because, but I was not enamored of the dining car. Cafe car options were pretty disappointing (they looked better on paper). I took a homemade veggie-heavy lunch and dinner in a small cooler for my first day, as well as some fresh fruits and lots of shelf-stable snacks, but didn't have time to shop for my return trip at all. I will be researching some homemade food ideas that don't need refrigeration or microwaving or hot water for my next trip. I'm thinking granola and shelf-stable milk boxes for breakfast will be easy. PB&J and tuna packs are obviously an option. But if I could get some vegetables in my second day, that would be amazing.
I felt pretty safe as a solo traveler. I kept my important items in a fanny pack that was always looped over my chest. If someone wanted to rifle through the bag I left above my seat and take my knitting project, bag of random cables, and snacks, or my dirty clothes from my suitcase on the luggage rack - well, it would be super annoying and upsetting, but not the end of the world.
Assuming I use all the segments available on my pass, these 4 segments were $120. The prices for refundable tickets on the day I booked my finalized trip was $520 (I changed dates once, love the flexibility).
I start trip #2 in 10 days...