I have lived in both cities. Both are good, but IMO Pitt is much better. To emphasize my lack of bias, let me say I am from the Midwest, then moved out West. I've lived almost everywhere incl overseas, so I don't think I'm being ethnocentric and narrow-minded. But Indy is much less diverse and has much less charm. This time around, I didn't interview in Indianapolis, but interviewed 3 sites in Pitt.
You can PM me if you have specific questions.
Both are very cheap. Pitt is the larger of the med centers...UPMC has nearly biggest transplant . Pitt WAS steel town, but anyone still saying that has been moth-balled since the 70's.
My opinion is that IN folks are a little nicer, but a little slower. Zero topography there...landscape is boring boring boring. Sand dunes, whatever.
Medmal is worse in PA, better in IN. This is historically due to IN having gov who was doc. But medmal doesn't affect you in residency, and much less in practice than everyone concerns themselves with on this site. Med ctrs have your ass covered.
Indy is more suburbia, Pitt more city charm, culture, restaurants much better. If you are from East Coast, you may feel stifled in IN. If you are midwest and never lived anywhere else, Pitt may scare you.
Out of 10, Indy gets a 5, Pitt a 7.5.