Most of the Amtrak routes outside of the DC to Boston northeast corridor have trouble staying on time. So you need to be flexible in your expected departures and arrivals. You, as a taxpayer, are also heavily subsidizing those routes so might as well reap what your taxes are sowing.
I have taken Amtrak long distance trains at least once per year for the past 30 years or so. I happen to really enjoy train travel, so I look at the experience as sort of a mini- cruise. I would spend the extra money and get a sleeping accommodation (if you are alone or traveling with one other person, the economy roomette is all you need; the bedroom can sleep two adults and two children). The roomette has two bunk beds.
The cars are double decked, with most seats upstairs, and toilets and showers being downstairs. A typical Amtrak east-west train conveys three sleeping cars (1/2 of one of the cars is reserved for train staff), a dining car, a “sightseer” observation car with all glass windows upstairs and a snack/drink bar downstairs, and three coach cars, each of which seating approximately 80 people in a 2 x 2 configuration, the seats have a very generous recline and have basically unlimited legroom (the NYC-Florida trains do not use Superliner cars as they do not fit through the Hudson River and Baltimore tunnels).
The food is hit or miss; breakfast is the most consistent meal on the train; their premium dinner item is a flatiron steak, unless they’ve got some daily special like crab cakes. The snack bar prices have increased dramatically; if you like an adult beverage, bring your own supply.
If you buy a sleeping accommodation, you get access to lounges in stations such as Penn Station in New York, Union Station in Washington, DC and Union Station in Chicago. These don’t serve complimentary alcohol (unlike, say, the Delta SkyClub system), but they do check you in for the train, have unlimited soft drinks and pretzels/snacks, and there is priority boarding (in DC, the lounge has its own doors leading to the platform). If you have trouble walking, they’ll put you in a golf cart and drive you out to your car.
As far as the ride, unless you are going between DC and NYC or Detroit-Chicago, where Amtrak actually owns the railway, you will be at the mercy of the large freight railroads that own the tracks. For example, on the DC-Chicago “Capitol Limited”, you leave DC around 4:05 pm ET and are scheduled to arrive in Chicago around 10:30 am CT.
For the first part of the trip, you are on the CSX network, mainly the historic Baltimore & Ohio route via Cumberland, MD to Pittsburgh. In east Pittsburgh, your train will shunt onto a short route running between the University of Pittsburgh and Carnegie-Mellon University to a point where it joins the historic Pennsylvania RR mainline. It has been my experience that the trains run close to schedule on this part of the trip, although it takes over 7 hours to go just 280 miles through the mountains.
The former Pennsylvania RR tracks are now owned by the other giant eastern railroad enterprise, Norfolk Southern. West of Pittsburgh, there seem to be significant bottlenecks, including over the Allegheny River just west of the Pittsburgh station, just east of the Maumee River at Toledo, Ohio, in and around a large marshalling yard west of the station at Elkhart, Indiana, and within Chicago. Your route runs along the north side of the Ohio River, then up the Beaver River, crossing into Ohio at East Palestine, passing through Salem, stopping at Alliance, switching there to the old Pennsy line running to Cleveland, then joining the former New York Central line just east of Cleveland station (which is in front of the Browns football stadium and Rock N Roll Hall of Fame), then through Sandusky and into Toledo, then through Bryan, Ohio, running along US 6 into Indiana, then northwest through Goshen, stopping in Elkhart and South Bend, and then covering the final 90 or so miles into Chicago.
Even Amtrak can’t ruin a great train trip. If you like to travel, try it once and see what you think.