If you knew someone was holding a ilegal raffle to get money to send their kid to school by raffling off a pair of thier season tickets, would you report them?

No, as long as the tickets are legit and minors aren't allowed to enter the raffle. Nobody is getting hurt, someone will actually win, and a young person might get an education.

Maybe there's a downside I'm not thinking of.

I'm the kind of person who balks at rules in situations where the rules become devoid of merit.

No, cause some child is going to get an education.