I really hope you change your mind Lax. Like Ualaa says a majority of the people who do this for the competitive nature do so to be competitive on the ladder and not just to participate against other boxers.
It doesn't help that a ton of people have canceled their subs and that a majority of people who might re-level for this sort of thing will be extremely far behind gear wise... but thats the nature of MMOs.
I want to say that although you are trying to invigorate competitiveness and a reason for people to PVP... so few people PVP'd to begin with since cata that I doubt a menial amount of money (not @ the higher amounts) will persuade them to push themselves. The community as a whole (including Tim's site) are just not active enough in this sort of means to have a prize pool and structure like that. Honestly you might be better off making the prize for top 3 and not limiting the required characters controlled to 5 but just more than 50% of the team in order to prove what multiboxing in arenas is capable of (confining yourself to all 3/5 really hurts your chances on the ladder and more so encourages grinding which a majority of the community does not have time for anyway). That being said if you do so it might be best to do one bracket with a combined prize pool to help motivate people more and garner higher participation. Not only that but a larger prize pool with a single goal will attract new boxers as well as possibly bring old ones back.
I won't be participating if I have to choose between ladder play and playing for money. So best of luck to everyone who decides to do so.
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