I think whatever the outcome, it would be nice to have some sort of clear definition of which team won and which team lost. Even if it's just a timeskip to the end of the session, and Wraith determines it. I think the Winners and Losers mentality amongst the students would be interesting and I'm fine with Freddie being either. 

I'm also in favour of a timeskip to the day of the dance, if that's on the table. It'd be a good point to introduce the new characters and a nice change of pace.