Now since you have them wear the item when it reappears,
anyway to get them to wear it if someone requests it
not knowing what it does, finds out they don't need it
and give it back?

I think that this new request feature may have accidentally made that possible to do. Previously, the issue was that it wasn't convenient to check whether or not what you handed to the NPC "belonged" to them. With the new code, it should be possible to check for a "queued" requested item and look for a match. I can think of some possible exploits for this, however, and I'll have to look into how practical they are to execute as a PC.

valguarnera@carrionfields.com