What smarter cities have done when buildings are no longer adequate to serve their purpose is to preserve the facades as to retain the character of the building and neighborhood, but build a thoroughly modern facility that exist behind the facade, sometimes with additional floors set back just enough so it not to interfere with the historic context from a street level view.
There are many examples where Pitt, in particular, has failed to take the architectural character of the neighborhood and campus into account. Not that Pitt hasn't done some amazing preservation work, like the the interior of the Schenley Hotel (aka William Pitt Union) and the Masonic Temple (aka Alumni Hall), but completely failed on some other things (e.g., the Logan Armory, globing the SRCC onto Thaw Hall's main entrance which had its most prominent architectural features, etc), and it threatens to demolish the Central Turnverein (aka the Gardner Steel Conference Center) and Concordia Club (aka O'Hara St Student Center). For every good decision, like renovating Schenley Quad to be pedestrian only, there seems to be a dumb one like removing more historically sensitive street lamps from around the William Pitt Union. The frustrating thing for me is that anyone that visits other universities sees examples of other schools incorporating and preserving their historic buildings into more more modern facilities all the time, and they usually end up being very special spaces on those campuses, but no, let's demo the Concordia Club at Pitt and build a generic modern office structure on top. Like what moron architect would even sign off on that for just being presented in a public proposal?
And why on earth can't Pitt get some uplighting on its historic buildings at night. Fine, don't want to leave them on all night if one is so worried about the electricity costs or some eco nonsense, turn them off at mignight or 3am or something, but my lord, they won't even turn on the existing uplighting on the Pittsburgh Athletic Club building when they bought it, which I've heard many unprompted (non Pitt people) comment at night on how cool the building was. Pitt has such awesome buildings and uplighting at night would really work well to highlight their features in ways that are completely different than during the daytime. I mean, they did add some uplighting to the Schenley Quad dorms, which is good, but there is absolutely nothing on the Cathedral's gothic features. And it just makes the streets so dark at night when there is nothing (the difference on 5th Ave when the PAA used its uplighting compared to when you walked in front of Alumni Hall next door was striking). I really don't understand some of the decisions, and I know they don't seem to be honest about some of their explanations ("oh, we didn't know the
Croation Fraternal Building was historic"...like you couldn't tell from just looking at it....these are supposedly architects for jebbus sake)).