The different route through PA may well be the reason for taking the #30/#42 route. Allows for a round trip between CHI and NYP with much of the daytime portion over different scenery in PA vs NY. They are probably experimenting with it as the longer trip time through PA with the layover in Pittsburgh may not attract as much business as the LSL route.Wow - just imagine, Horse Shoe Curve and rural Pennsylvania. Not to mention, departing NYC and following the Hudson up to Albany. What a ride.
However, it should be noted that they are not saying anything about the route to be taken in either direction. The CHI-NYP service starts November 1. There is a possibility that Amtrak plans to flip the CL and LSL departures from CHI in the fall schedules, but that because it is not official yet and can't be published, Pullman is using the #30/#42 times as placeholders.
On the cost of the restored cars, checking the one page equipment description, they probably spent a fair amount on upgrading the cars with installation of showers, update to modern safety standards, modern amenities including WiFi, power outlets. With a 2 day a week schedule, they will have time to service the equipment; in Chicago it looks like from the schedule.
As for using this to substitute for an Amtrak sleeper car on the LSL, Pullman is providing a high end niche service. They may well attract clients who would not normally consider taking Amtrak overnight between Chicago & NYC. Different market strategies and segments. A big difference is that Pullman is taking passengers on board only in CHI and NYP. Can't get on Pullman in Albany, Buffalo, or Philly and Pittsburgh. That may be a market mistake on their part to not take on passengers on at least a couple of larger market stops in-between. This is such a different type of sleeper service from Amtrak offers is that it makes no sense for Amtrak to adjust their Viewliner sleeper assignments based on a 2 day week premium service schedule.