Not really my most memorable one, but I did ride the Southwest Chief from KC to Chicago a couple years ago. I liked that it was a pretty direct train - 7 hours with only a few stops, faster than driving. We were staying downtown, so not *too* much slower than flying. I was not prepared for both the lack of Wifi and poor cell coverage during the journey. Nor did I care for the painstakingly slow and manual boarding process for the train. In Kansas City, you have to physically stand in a VERY long queue inside Union Station for 45 minutes and then single-file walk out to the platform at a specific time, where a conductor manually assigns seats. Amtrak has mobile tickets, but that didn't alleviate the need to queue, thus killing any value of having mobile tickets. We were also unable to pre-book a dinner reservation in the mobile app, meaning we were subject to whatever was available when the conductor passed through our car taking reservations.

(Dinner itself was not very good, but we were highly amused by the fact that menu appears to have not changed since at least the 1970s. Salisbury steak with mashed potatoes, anyone? You just gotta do it once... )

If they implement process improvements that allow me to park and walk directly to the platform with a preassigned seat and ticket loaded on my phone, I'd totally do it again. Even with the spotty cell coverage along the route, it's a relaxing way to travel if your end destination is downtown Chicago. But I won't do it again if there's any risk of being stuck in that queue.