Fellow, regarding point 1, i might have an solution.
I think that instead of cancelling the "bartening" and then dropping the axe for yourself (the same way you've picked it up) you are giving the axe to the person you're bartening with. So the villager says "okay, so there's no deal? well, i have the axe now. You won't carry unpaid items anymore"
The problem then is that the person, even carrying the axe that was in the floor, might not will to trade it away.
Tell me if that was the problem with the "misterious vanishing" of the item.
Good trips!