For anyone who has similar issues... After a couple days of messing around;
I am guessing manifest_version 2 requires stricter associations.
With my last screenshot as reference:
Delete the entire "web_accesible_resources" block.
Delete the entire "key" line.
Change the "manifest_version" to "3,"
Loaded fine.
This is probably a janky solution? idk if it will cause any issues elsewhere. 

