Took a train from San Antonio to Buffalo one summer about 15 years ago. Sleeper car's the way to go. It had a "sightseer" lounge car; 2nd story observation car. Took in some scenery while getting liquored up. Got in to Chicago late for my connection train to Buffalo which ran daily from 7 pm. Amtrak put me up in a hotel. Next day was "Taste of Chicago". Huge party. Had some fun before departing at 7 pm.
By the way.....Amtrak is almost always late. Freight has priority.
Next trip was with a buddy of mine. Flew to Buffalo for a football game and had tickets to next game in New Orleans. Then Katrina happened. At least game was in San Antonio, so the trip was still on. Although football seats weren't nearly as good as the ones we had in NO.
Train crashed just outside of St Louis. Pretty big wreck. No deaths but several injuries. Had to stay overnight and ended up flying to San Antonio on Amtrak's dime. Actually got to San Antonio about an hour before Amtrak's scheduled arrival.
All in all, trains are fun as long as you stay on the track. Food's good too. Keep in mind, if you get a sleeper car, for a single person, it costs more than flying and takes about 10 times longer.