Am i the only one who has a problem with OP offering money (being that in the form of a giveaway) in exchange for participating in flag support/opposition? WTH, really?

As long as the payment isn't based on the outcome, and the reward is public, I think it's okay. It's different when people pay for for positive reviews or negative feedback (I've seen both cases).
It's certainly a first

That's not what the trust system is for. At best this is low-effort spam, incentivizing which is against the rules when posting on the forum, and I can't think of any reason why such incentive could be good for the trust system.