Stranger things have indeed happened!
If I were a McCaskey's I'd simply clean house. The dream scenario would be JA and the entire coaching staff would be gone. I'd hire Mike Shannahan and let him act as GM and HC. But woul require he bring in some personnell guys and scouts, and that he try not to run everything. I want him coaching primarily and really getting the offense, and in particular, Cutler up to par. I let him hire his own staff. I would leave Teddy-boy alone and basically keep him as a finance guy only. Let Tim McCaskey be the face of the organization as CEO or some title like that.
Let Shanahan make the moves he thinks he needs to make.
I'd push for certian things, like the following, but would ultimately let Shanahan make the call:
1. Move to 3-4 D
2. Get rid of dead weight, and try to get picks for some non-dead weight (like Harris, maybe Briggs, etc...)
3. Get some better OL in FA and expect to draft one early
4. Try to bring in a vet WR that is a big target
5. Bring in a bruiser RB that can get hard short yardage, like a Crockett form OAK a while back
6. Demand tough play from the D. We only want good tacklers.