Another suggestion thing.
In roleplay, the monthly battle records for every student should be public knowledge and be displayed somewhere in the form of a ranking system.
For example, maybe there is a big fancy screen in a hallway everywhere. On this screen, they list every student by their name, picture, and W/L ratio for the month (with all-time records being confidential).
So everybody can see that Mary Sue is in first place with a record of 9-0, with Gary Stu and Barry Lew trailing behind with tied records of 8-1. Meanwhile, Ebony Dark'ness Dementia Raven Way is in last place with a horrid 2-7 record.
The person at the end of the month, along with the privilege of battling the guest, should get a reward of cash or items. The point of this is to make the site and school really competitive, so people are constantly trying to climb to the top of the list. It provides a good incentive for people to seek big-winning trainers (or big-losing, if they're cheap) out, while also explaining why they know the other person's records and who to look for.
Here comes the second part of the suggestion: bounties.
Gary Stu is still in second place, and it's now in the middle of the month. He has to get ahead of Mary Sue if he wants to be in first, but he doesn't want to risk losing by challenging Mary Sue herself. Instead, he posts a bounty in the hallways, promising 500 Poké to the first person who beats Mary Sue. That way, he doesn't have to suffer the fallout if they lose and only has to fork over some money if they win.
It could backfire, in that if Mary Sue successfully defends her title against all the people hunting her, her win rate will bloat, but that only makes it more fun and dangerous. ;D
What do you think?