As I read the OP, the "worst case scenario" training-wise is maybe eventually commuting 14 miles/day, 4 or 5 days/week with not even one long ride loaded. If that plays out, you might want to re-think things.


Note that you could shorten the trip by using the Amtrak. Start in PGH, ride to Cumberland over how many days and take the train back to PGH. A reservation for one of the limited bike spots on the train would be wise. Not the most appealing this logistically because the train does not arrive in PGH until late at night, but there are a couple of hotels within a block or two of the station.