You look at a school like Miami...small, urban, private...in a city that really isn't sports crazy. In a lot of ways, a lot worse off than Pitt.
But Miami has found the donors to come together to go all in with this stuff. It's not even so much the university really approaching things differently, its the donors coming together to take advantage of the new system. Every single school is forming these NIL entities, but Miami has found the people to really go all in. To be honest, the university just needs to stay out of their way.
I can't predict the future. Maybe there are enough people that this wakes up and come together for Pitt. I wouldn't put money on it, but I'm not ready to write things off entirely.
For a while, since BYU did it years ago with their soccer program, I've seen the potential for a true professionalization where athletic departments become their own separate legal entity and just license the university name and images (just like UPMC does with Pitt...affiliated, but legally separate). The players then are just employees of that athletic entity, there is no need to attend school at all, NCAA doesn't apply, and title IX doesn't apply. What is going on with NIL just makes this more likely in my opinion, but who knows if it will go that far.
What happens in such a dystopian future?..ND has always stated if things get professionalized, and players become employees, it won't join the professionalizing schools. I think you may see a split between the SEC-type schools and the NDs of the world (if you can believe that their boosters won't force them otherwise) to form a more academically oriented group with schools like BC, Wake, etc.
Where will Pitt fit in? Pitt is sort of an in-betweener IMO. It would really depend on how Pitt is fairing in the new landscape and on the univeristy's leadership.
I can tell you though, the selection of Pitt's next chancellor is going to be huge for athletics in this landscape