The more I think about this the more I like it!
If I remember correctly Jim's samson posts go through the deck and are bolted to the bulkhead just like the wooden ones, I chose to do it a bit differently... mine are welded to a plate that is part of the mount for the whole assembly and there are no penetrations through the deck except the chain pipes and mounting bolts. The bedding for the samson posts was a continual source of leaks so I eliminated them!
There is no reason the sprite has to be made just like all the others! Maybe tapered... widen it out a bit to mount the windless and narrow it a bit on the end to save a bit of weight...
A round penetration with a tube welded vertical in the square tube for the drive shaft to pass through should be no problem as far as strength is concerned as it is primarily a compression load.
The other question is will the motor location which will be determined by the chain pipe location fit in front of the bulkhead... I suppose one could always make a cutout for it if need be though.
More later... back to work!
Steve