I grew up in Syracuse and have family in and around Pittsburgh. The difference in size does make it difficult to compare the two. To the OP, some of what you want in a city is going to depend purely on the size of city you prefer.
I just think its unfortunate that both cities have been given a bad reputation as "rust belt" cities primarily due to the difficult economy both have faced when industries fled south. Both cities have a lot to offer and are great areas. Both areas are trying to make a comeback after loosing those industries and I think both cities are doing a good job of it, slowly, but still making improvements.
If was funny, when "ainulinale" posted the orginal photos of the city of Pittsburgh at first I thought they were photo's of Syracuse. Primarily because a lot of the old architecture found in Pittsburgh can be found in Syracuse, just not as much of it. It wasn't until I saw the photos of taller, more modern buildings mixed in with the old buildings that I realized they were pics of Pittsburgh.
By the Way, I hope Steelers kick butt this Sunday