My idea is regarding the Briefcase.

It seems 99.9% when cashing it in you're going to win. I think if someone were to cash it in, put it in the results and have the rest of the results (or just the match) and give both the Title Holder and Briefcase Holder 24 hours to do MAX 1 roleplay each, then whoever judges .. judges those rps to declare if it was successful or not. Of course if the title holder is out of town, or can't rp due to work during that 24 hours, then they lose. That's a plus/mysterious part about cashing in whenever.