It needs to be pointed out that, in winter (which this trip is), the New River Gorge will be in darkness on a westbound train. Taking the Cardinal eastbound would give you the scenery. Westbound, you will get some pleasant scenery in farmland, but it will be dark by the time you reach the New River Gorge.
I have taken the Cardinal eastbound since they put in the wif-fi. It worked adequately (if slowly) for low-bandwidth needs like checking email and light browsing. Transferring attachments would probably work, if they are not too large. There was no wi-fi signal at all in the New River Gorge, due to the terrain. I'm assuming no one's cell phone worked there either! But I would not have wanted to be on my computer at all in that portion, because the scenery was so beautiful. The big advantage to doing that trip in winter is that you can see a lot more of the river when the tree branches are bare of leaves. Your Dad should download a map of the Gorge on his ipad before you lose your signal.
If you are doing the trip in both directions, and the wi-fi is important to you, I'd go for:
westbound: change at NYP. The Lakeshore Ltd has wi-fi now, correct? I hope so, I'm booked on it this winter!
eastbound: take the Cardinal from Chicago to Washington.
In either direction, if your train is running late, and likely to miss the connection, they may re-book you automatically on a train with a longer connection window. But barring a nasty early winter storm, or freight incident, you are quite likely to make all your connections.