Sounds like a good idea to me. It'd certainly beat the usual 'I'm better' rubbish.
I think you'd need to limit the challenge to CR crews though. Each type could have a specific role such as point defence for fighters, bombs on tgts for the muds, evasion and collection for the helos and pies eaten in and hour for the truckies. You could post the results here for everybody to see like....
25 Sqn vs 31 Sqn:
25 Sqn 2 kills out of 4 (2 points) 31 Sqn 2 a/c over target (2 points)
Keep a rolling score and the Sqn with the best average wins the coveted PPrune trophy
(and 2 months in the Gulf!)
I think the Chinooks would do quite well, always been impressed with the way they fly along motorways to confuse the radar picture.