Cool idea. What do you other coaches say? Well we seem to be discussing 2 separate things, the idea of a cup, and the possible rewards.
So I will discuss both separately.
I am fairly indifferent to the cup idea, it is not a bad idea, but a few issues need to be sorted out.
How does this affect buying rules, can you buy players before the cup, and then again before the next season proper?
What happens if not every one wants to play?
Say if 6 wanted to out of the 8, then for a knockout format you would have to go to 4 players and start with semifinals.
In that case who out of the 6 miss out?
Also I could see it feeling a bit weird if we just had knockout playoffs from the league proper, to then go straight in to a knockout cup.
The possible Cheerleader\Assistant Coach rewards seem to be discussed as possible for a cup and future league season, so will cover both.
Not particularly keen on this idea, seems contrary to the whole idea of banning them in the first place.
Also the team winning the league\cup is likely already one of the better developed sides, and now on top of that you want to give them an extra potential advantage.
There is already a large disparity between the top sides and the bottom sides.
That brings us on to the idea of giving the bottom side a reward to help them.
There is not much difference between coming 7th or 8th place in the league, but in the suggested scenario you are better off being last.
Real world example, if Parrigan wins his last match he will jump me to 7th, if he draws or loses he stays 8th.
There will only be a point or two in it either way, and neither of us will be going to the playoffs.
Now in the suggested reward scheme he is actually better off long term not even trying to win, which just seems wrong.