phughes, did you ride my route???
When you say hilly route out of PGH, do you mean the Montour / Panhandle trails, or a road route which is further north? Or do you mean the mountains of eastern Ohio? I've got the Ohio section broken into 2 days, but I'm depending on the rail trails to get me to the Ohio border with moderate effort. The nice folks on BikePGH helped me with that part.
The Bug is a scary unknown. All my stays are cancellable with short notice, just in case. Indiana is opening on a limited basis Monday, so we'll see how that experiment goes. If there is a resurgence this fall, they may close down again, and the party I am riding to will be cancelled anyway. Luckily solo bike riding is one of the few sports left to do, so I can keep training. Even if I cancel I will get to do a lot of riding, so that part is a win/win.
For the record, that 91 mile day can turn out 3 ways: I do it and pay for the next 2 weeks; I crash in French Lick where there are numerous hotels; I call the SAG wagon which will be in range at that point. I'm trying to have options and not bet on one horse here.