Okay, and just so it wasn't a fluke the other times. I have refined the error messages and can confirm the sequence of events are what are messing things up.
if PLAYER_LOGIN is triggered last it will load properly. If VARIABLES_LOADED is triggered last it will load bad.
The unfortunate solution is to use ADDON_LOADED to do data preparation and PLAYER_LOGIN for displaying etc and VARIABLES_LOADED to override positioning and anchoring that blizzard sets up from their variables.
And the reason there is no error message is because nothing is going wrong. A for loop will just not execute if there are no items in the list and so thus the tests later on silently fail.
But then thats my theory.
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