I would think a 4 hour lay-over is sufficient and certainly allowed (1 hour minimum), but the Amtrak web site just has percentage of arrivals on-time, which isn't good for train 49. But does that mean the trains average 1/2 hour late, or 6 hours late? Maybe someone can comment on that.

The discount is per person, but if the daughter is not 62, AAA is a discount, as are others. You probably can book on line and then call for info. I think I have when circumstances changed after booking.

As far as accommodations, the ear problem could qualify. They don't ask what the problem is, so just ask for it. Remember though that the HC room is on the lower level on the Zephyr, while the diner and lounge are accessed though the upper level. Does she plan on staying in the room for 2 days and having the attendant bring meals (be sure to add that to the tip), or does she not mind climbing stairs several times a day?

They have red caps in Chicago. They will meet the incoming train and take you to the outgoing one. Tipping is always recommended. Let your conscience be your guide, but $1 or $2 for two people and baggage is definitely not enough. Sleeping accommodations are what qualifies you for the Metropolitan lounge. You can always check bags, so long as they are under 50 lbs. each, unless you need access to them. Then either keep them in the room or down the hall in the baggage rack.