Personally I dont think that Darryl should coach again, but that would put me in the minority around town. Most fans in Calgary think that if Sutter coached again we can just stamp out ticket back to the cup finals. I think people choose to forget that in 06 Sutter was the coach when we lost to the Ducks in the first round after winning the division. I think that Sutter likes that most people consider him a god and if he coachs and fails people wouldnt think that anymore.
Also, I think hiring an assitant to help manage the team so that he can focus on coaching would be like giving himself a demotion. He is somewhat of a control freak, and I would be shocked if let someone else take over some of his GM duties. That is why he was hired as a coach and GM in the first place. He has to have full control, look at his two hires, Playfair and Keenan, they were both his puppets, and I doubt that Playfair in particular ever had control of the team.
The only scenario where I could see Sutter coaching, would be if they fire another coach part way through this season (ala Lou Amirillo in NJ a couple of years ago). Otherwise he would have to pay 3 head coachs at once which would look ridiculous.
I would like to see a new head coach come in, and fire all of Darryl's assisitants, and bring in his own. And give the team a new direction. Preferably a defensive direction, make Kipper into a vezina candidate again, instead of leaving him out to dry like we did for the last 2 years.