Why can you place a Tribute chest normally in a raider outpost and it still works once you've turned it into a regular settlement but that doesn't work if you just put it in a settlement?
No idea unfortunately - likely the way it's been programmed. Similar to the vanilla bug of the Pick Me Up stations not spawning new items if you visit a settlement/raider outpost and don't empty it completely each time before you leave (see the Fallout Wiki page on it for details).
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Oh my gahhhd....