Just my opinion but I think the team has been down quite a while, that I think makes it tougher. Take a look at Miami, they make a little run, suddenly they have $400k to throw at a kid. So it is certainly a catch 22 in a way because in todays CBB landscape you need to spend money to get kids, well how do you get donors to want to spend money, its by getting good kids and winning. Can't have one without the other whether you like that or not.
The other thing I personally think is this NIL thing being a bit of the wild wild west, I think up and coming companies want to get out ahead of it and be a pioneer of it. I think established companies like say Target, Best Buy, General Mills etc I dont think are rushing to pay an unproven 18 yr old kid a few hundred thousand dollars when they can put that into naming rights of a stadium or a known quantity.