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Not sure if this is what you are referring to but sometimes this info gets buried disappears over time thus do not advance.
Explained here
Quest Journal Limit Bug Fixer - Recover Disappeared Quests
https://www.nexusmods.com/skyrimspecialedition/mods/56130
Take a look and see if this sounds like your issue
Someone may come in with a suggestion in the mean time.
There is a list on the wikis of AE content, the items usually contain links to pages on the quests, including how to start them.
I went and checked UESP one more time and it did say you need to enter that shop at least once to trigger the letter. How anyone's supposed to know that without looking it up is beyond me. I literally never go in the Drunken Huntsman unless its to kill the hireling to power the Ebony Blade lmao