Re: Looting a Hireling that's using an Item
This is by no means an official response, but I interpret that situation as follows:
The Thief Hireling says that the abilities of the Boomdagger count for you. Steal a Hireling (or similar card) takes your Thief Hireling away and the Hireling rules state that the Boomdagger goes with him. As the Boomdagger's ability counted for you when it was taken, it would count as being stolen and would come back to you on your next turn. However, if you are not a Thief, you would now need to turn the Boomdagger sideways as you cannot use it. If the Boomdagger is lost again before you find a way to use it, it would not come back to you (as it needs to be equipped for its powers to have any effect).
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My unofficial, but comprehensive Flowcharts: Munchkin: A4 Letter; Munchkin Quest: A4 Letter
Rules Checklist for all Munchkin sets: A4 Letter.
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