I only skimmed over your post, sorry for not reading the whole thing yet.
But off hand, make sure you load your custom window to the UI memory with a "show_window Custom.LlamaDebug" before you modify anything with it.
When you access windows in the UI memory, you don't have to include "MainHUD" or "Custom" when navigating the tree.
For example, for the Persona window to access the guild window you just have to go Parent.Guild, not Parent.Parent.MainHUD.Guild
You CAN access certain windows with the longer way, but that's only for windows like popup windows who's data gets reset each time they show.
All the Top Level Objects disolve into one shared object in the UI memory when the game runs.
Hope that makes sense.
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