Anyone know what this is?

Tile cutter, I have one identical.
You place the tile one the cushion pad, grab the handle, then drag the little cutting wheel across the tile to score it. Then you slide handle to middle of the tile, push down so the two little wings push down and the tile should crack in half on score line.
Nowadays, most people use electric tile saws.
 
Interesting. I don’t see him having any reason to bore holes in barrels or trees. Maybe someone gave it to him, or he was using it for something else.
 
If it is a smaller / shorter one it could be it was used to create a tapered hole in old damaged wood flooring to drive doweling or a cork in before laying down new flooring. Nail holes or small imperfections could be bored with the tool, filled in with a piece of doweling or a cork, cut off flush and sanded smooth to provide a good base for a new layer of flooring. Just speculation on my part.
 
When I was in Spain many years ago they stored their wine is pig skins. The skin would be stood on its butt in a rack with a spigot like that in the left hind leg for refilling their wine pitchers. Would be tied tight with several wraps of cord of some type. Very primitive back then. Early 60's.
 
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