[CWuestefeld]

I went NY->Chicago->SF, the reverse of the route in the OP. We were held up for about 3 hours in Helper, UT, due to a washed out track. It was a really positive experience. Many passengers were gathered in the observation car, and one guy had a guitar with him. We spent much of the time having a singalong.

And once we got past the washout, the train was positively flying - we made it into SF only about 1/2 hour late.

I loved pretty much the whole thing. High points were watching the scenery, and also interacting with other passengers - both in the observation car and, as the OP notes, at meals. But I'm really glad we did it "1st class" - that is, with a sleeper cabin. This was comfortable and quiet, and provided a way we could make it "our experience" when we didn't want to be stuck with the rest of the crowd.

The sleeper car is much more expensive, but includes meals. All told, I think the price of the three day trip including sleeper cabin and meals, works out similar to airfare plus hotels and meals for a similar time period.