I'm going to make a hard call here. I think this is the tail wagging the dog, and Amtrak should *not* have a "cleanup train" for late western trains. This is wasting a valuable Chicago-East Coast slot on assisting the money-sucking western Transcontinentals. If there were an independent business case for a train departing Chicago for the east at 9:30, that would be a reason to do it; "collecting passengers from delayed Western trains" is NOT a good reason.
I would guess it would be unrealistic to not have a late train (around 9:30pm) going east.
We've already documented that a supermajority of "Chicago-East Coast" passengers do *not* connect from *any* western trains. (A fair number connect to the corridors, but we're not worried about those trains being super-late.)
LSL ridership was predicted to go up by 10% or more by changing the schedule. Is it really worth losing 9% of your riders on a *relatively successful* service, in order to avoid overnight stays and hotel bills for customers on your *less successful*, *lower-ticket-price-per-mile* services? I say it isn't. They don't hold the Silver Service for late trains coming into NYP or WAS. They should dispatch the LSL at an appropriate starting time and not hold it for Western trains.
I will also point out that people taking most of the Western trains long distances are not in a hurry and can afford to spend the time overnight in Chicago in case of a late train. People riding a short distance on those trains, like from Denver or Minneapolis are an exception, but they are already dealing with their train arriving at their starting point late, and have time to find alternate transportation if they're in a hurry to make the Chicago connection.
I'll tell you what railways USED to do in situations like this.
(a) The railway owned a hotel located in the station.
(b) When getting news of delays that day, the railway would block out rooms in the hotel for delayed trains.
I don't know if Amtrak could set up a partnership with a hotel company and do this, but it would be better than messing up another train's schedule.
It sounds like you want the more "connected corridor" approach. Nothing personal but I hope that doesn't in general happen. I think for the most part CHI works. I have been past CHI three times (all Southwest Chief coming east) and never missed my East Coast train (twice Three Rivers, once Capitol Limited). I hope we don't get to a situation where if you want to get from the East Coast to California you have to make 2-3 transfers as opposed to the 1 now (honestly I'd love it to be 0 but that might not be realistic in 2015). That would give you three chances to miss a connection as opposed to one.
I get that the longer a train the more delays there are. I want the CL/Pennsylvanian to happen but I understand PGH residents would prefer not to have to wait for the CL to come from CHI to travel east. If PA DOT does come through with the second PGH to NYP train, I think that will help PGH passengers to give them a train that does not come from CHI.
In terms of the LSL leaving early, I guess I would prefer to leave a little bit earlier and arrive in NYP before 6:23pm (I have a feeling that the next time I travel to CHI from PHL I will probably take SEPTA/NJT to NYP and then the LSL rather than use the CL). But I'm not going to fuss too much over the times. If the LSL leaves CHI three hours early as proposed it would get to CLE around 2:30am which I would say is far worse than 5:30am and it would get to BUF to before 6am. I'm not saying the shift is wrong. But if you shift a schedule, there's winners and losers.
Let's go to fantasy world now. If there was a BL AND a LSL, one can be a train arriving at NYP before rush hour and the other can be the "cleanup train". Or if you have a CHI-PGH-PHL-NYP on a schedule where it would arrive in PGH before midnight and arrive in PHL the next morning that could help passengers who get stranded in CHI. So if the LSL leaves at 6:30-7pm ish and you miss it, it still sucks for you. But if the CHI-PHL-NYP train leaves around noon the next day as opposed to 6:30-7, it's still six hours better than now. So either a new BL or a "Skyline" schedule that goes CHI-Ohio in reasonable hours would still make things better and help move the LSL earlier.