"Da U" hasn't been any good since 2003. UM players in the post-Coaker era that are in the NFL shocked pro coaches that they couldn't even watch game film properly. This looks very bad for the program. It was barely above average at its very best within a weak ACC conference where they've yet to appear in an ACC championship game.
I'm of the opinion though that the NCAA should ditch the damn rules. If a booster or anyone wants to give a player money, let them. If there is any criminality involved in the matter, let law enforcement handle it. The NCAA in its present state cannot enforce the myriad number of obscure rules and universities shouldn't be held accountable for what players do on their own time. Its a university, not a daycare service.