Do you look like Wendy (from Wendy's)? You know with the redhair and the big red cheeks? Put your hair in braids and let us be the judge!
My boss is a pain in the butt but also one of my best friends, so I do crap like that to him all the time. It's ok because he does some pretty bad stuff to me as well. I think you should go for it. Get the keys to that bad boy and go for it.
Do you have anything news about hot contractor or are you waiting for him to come do the job and then going in for the kill?