You may be overthinking this. You only need to draft an authority figure or commentator if you intend to use them on the advertised card. If you would feel a need to advertise a card and put on the ad "With commentary by Jim Ross", you'd have to put Jim Ross on there. If Ross is implied to be on commentary and you don't say it, you don't need to draft him. If you put "The Executioner w/ Paul Bearer vs. Vince McMahon", you'd have to have all three of them drafted. Unless you are using somebody as a guest referee, you don't need to draft one. I wouldn't advertise Tommy Young, but if I used Mick Foley as a guest referee, I would certainly advertise it, thus I would have to draft him. I hope that I things, please let me know if I didn't.
Edit: We don't have to draft bookers, but if I wanted to have Jim Cornette vs. Vince Russo in a tennis racket on a pole match (which would count as one of my three stipulation matches), I would have to have both of them on my roster. If you're not advertising somebody, then they don't have to be drafted.
