You will have Title IX problems as soon as the school is directly involved paying players. No school receiving federal funds can provide a benefit to its male football players that it doesn't also provide its female field hockey players.

Personally, I also feel that boosters have too much direct involvement in athletic departments as is. Removing the school from the booster-player relationship and bringing booster payment to players out from under the table could potentially help clean up some of the corruption in college sports.