how is food (lunch/dinner) handled on the trains like this... someone mentioned seatings?
i assume they have two train drivers...?
If you took the LSL to Chicago, and you went coach, then things could be very different for you. But assuming that you get a sleeper like the title suggests, then under the old way of doing things you would go to the cafe car and show your ticket to get something for lunch. I haven't yet heard that Amtrak has resumed that practice now that they've restored sleeping car service, but I would expect that they have done so.
Dinner will happen after the Boston section combines with the New York section in Albany. They may give you a specific time or they may just send everyone in the sleeper down to the diner at once. Breakfast will be first come first served.
You'll arrive into Chicago before lunch, so lunch will be on your own in either the station or in Chicago.
Now if you return on the LSL, the you'll also need to do dinner on your own dime in the station. You will have a wine and cheese tasting upon boarding, but no real food unless you go to the cafe car and buy it. Breakfast will be first come, first served and they generally do the same for lunch, which is an abreviated service if the train is running on time. For dinner, you'll be back to the cafe car, which again I'm assuming that you'll just show your ticket and be able to pick from the items in the cafe.
Should you return on the Capitol as someone suggested, then you would get dinner out of Chicago. Reservations are usually taken when you check into the Metropolitan lounge, but can still be obtained onboard although prime times may be gone by then. Breakfast would be first come fiirst served, and lunch is usually the same and once again abreviated if the train is on time. You'll have to buy dinner either in the station in DC or onboard the NEC train in the cafe car.
As for engineers, it depend on where the crew change points are. Some streches there may only be one person in the cab, on others there will be two.