Hey There,
a) To answer your second point on the Chairman: They have 4 candidates who are coming back for second look, all very strong from what I hear from "insiders" and there should be a chairman maybe even as early as before the match. So by the time we'd be looking for fellowships there will be someone there to make the phone calls or pull for you.
b) To answer your second point regarding the PD. I think you do have a valid concern/point. He has been the PD for about 25 years! This is good (stability, must know tons of people nationally) and bad (stagnation) and he doesn't seem to have the zeal/energy that I have seen in a couple of other programs/PDs. But, when talking one on one with him (which I have done) he states that he will go to bat for you in terms of fellowship placement. Is it true?-I don't know. The program is now smaller (they cut it down to about 35) so I think he will know you pretty well, but it is true that the residents are in 3 different hospitals (VA, Shadyside for Cancer and Monty/Presby), so it is not like at some schools where you are always in the same place and so you bump into the PD more often. Overall, he is probably not the most personable PD, but exactly how much that matters is hard to say.
This is just my take as an MSIV at Pitt.