I drilled a couple of holes on Simcoe today as part of a Simcoe Ice Drilling Team outing without much trouble. It was hardly worth taking the drill for the sake of a couple of holes but I wanted to try it out a bit more than I had. The chuck just came loose once. That was when I put it in reverse to get it back up from the hole. I drilled/lifted/drilled/lifted as Brian suggested above.
The main reason for posting the pix above was to tell others of a fairly easy way to attach the drill to the auger: A number of people expressed interest in Brian's conversion but most of us don't have some of the tools that he used----e.g. welder.
The wood piece to stop the auger from dropping thru the hole is to me , of secondary interest. There are many ways of skinning that proverbial cat. The wood slides down the shaft under its own weight and sometimes spins with the auger. Yes, it's a good idea to keep 'vital parts' away from it , but it can be stopped from spinning with very little force because it's a loose fit. A circular piece of plywood would look neater but would take up more space when stashing the auger unto the toboggan.