I've taken 4 Amtrak trips in my life, 3 basically ruined the trip.
First, when I was a kid we took a train to Chicago from Michigan and for whatever reason we checked a bag. They lost the bag with my favorite stuffed animal in it and I remember spending most of that weekend crying.
Second, we tried going skiing in Whitefish Montana from Seattle and they made us take a bus to Spokane to "get the train back on schedule." We were something like 7 hours late getting to Spokane because of traffic and snow (not enough snow to mess up the train) and we missed a full day of skiing on our 2 day trip. (There'a a LOT more to that story that made it even more ridiculous.)
Third trip was from Seattle to Portland and it went fine.
Final trip was from Seattle to New Mexico. I had the time and figured it would be kinda cool to see the country by train. The first leg of the trip to LA was actually pretty fantastic, but shortly before arriving the second leg was canceled because one of their bridges burned down in a wildfire near Palm Springs. I realize that was a freak accident but they offered zero help and I had to scramble to find lodging and eventually a Greyhound bus to my destination.