One is the size of the pile of money you are willing to pay lawyers to enforce it. Because there is no software license enforcement agency that is going to sue neerdowells on your behalf.
The other is excluding good actors who don't want to deal with it. Obscure licenses increase the number of good actors who will forego using the software because parsing non-standard licenses is work and raises questions about the competence and/or motives of the developer.
Obscure licenses don't protect users. Good luck.