I'm with you, I don't know how they didn't anticipate how chaotic NIL was going to be.
I'm probably giving the NCAA suits entirely too much credit with my comment, but what if they purposely created a free-for-all situation with NIL to prove a point regarding their long held opinions about amateur athletics? For example, they could easily have set a cap on NIL (say $100,000 maximum, cash or items), but they didn't. It would have been easier to monitor without creating a mercenary mentality situation for the athletes. Any proven violations could lead to punishments just like were administered before NIL. But it's probably too late now to put in reasonable regulations because of the situation you mentioned about challenging the rules.