Instead of getting the relevant quest items, I was given dried rations twice (Imp and fake guard) and a minor healing trinket (Spinning Groat guy). The server reset before I was able to turn the quest in and confirm if it was possible to complete, but this might need to be looked at.
I managed to succeed in all of the checks also and return. The npc says you have nothing for him and you get no quest reward. The intimidate check on the dwarf love letter quest similarly hands you random items that don't seem appropriate such as meat balls from another delivery quest.