He looks comfortable enough on the mic and at least he makes the Full Nelson look like it hurts. But it's still a repackaged gimmick, with the repackaged Hercules/Billy Jack Haynes storyline and the repackaged 'offer plants in the crowd a chance to get in the ring and make the marks think they could be picked' deal they've done before.
I agree with everyone else though, $1,000 is plenty to start this. It's booked so that as Masters' confidence grows, he puts more and more on the line. Hopefully when he loses, they do some skits where he's flat broke from losing $20,000 or some such amount when it's finally broken.