I actually do have a stable up. The M.A.D. Organization. It did have 4 wrestlers in it, but they've left and I've restocked. Right now it's just Doctor Claw, Rick Martel and Mark Callous. I was thinking of throwing Rude or Ricky Santana in as the 3rd wrestler.
For the scheduling, I've actually don't something similar to fantasy football schedules in the past for my "performance over popularity" promotions. I set up a promotion/relegation system and had equal number of workers in each push. I would have everyone face those in their push once over several weeks. The Opener with the best match average would move up a spot, the Lower Midcard with the lowest average would move down, and so on up the card. Each "season" would usually take 2-3 months. In the default universe, NOTBW is great for that set up.