It sounds like there’s a low chance of it occurring, so we’ll make a record of this.
The Crafting Table is a type of machine, so it will count towards the feat.
Can’t reproduce this. Tested this by crafting a Door Piece, Trampoline and Trapdoor piece (all of which required Timber) using the Workbench and I received XP as expected. What item(s) were you crafting with the Workbench at the time?
Were you doing anything outside of the objectives (as in did you briefly go off to other things away from the objectives)? Due to the increase in XP, it could be possible that you’re getting more XP by the time the objectives become available.