with the sleeper car you get 3 meals a day. Not bad. The steaks are especially delicious. I tipped 5 dollars for the car per day. Might be cheap, dont know. I tipped dining car 20% of the menu price. Not like a cruise with the same staff, on the train they get off. so you tip daily.
Remember you can bring anything on the train. Beer, alcohol,wine for dinner (tip for corkage), food etc. For me, I find that when you have the sleeper you tend not to go to the observation cars. Go there. Its much better view wise, comfy, and the people are always nice and friendly. Also in the bar car, its a pretty good party. Late night is at times raucous.
WIFI is at times spotty. Its better but not dependable, no matter yours or theirs. Be sure you have headphones and a bunch of media loaded on your devices.
Chicago is a huge transfer spot. Get to know the station before you head out so you are not stressed and in unfamiliar territory. Most trains give you a few hours in Chicago, Denver and other stops. The rest you get a few minutes. Now you must go off the station to smoke. Anything. Most stops dont allow the time. (If you are a smoker) The great thing about the train is the stations are right downtown so, on the longer stops, you have time to do some things.