If you poke around the Full Category Tree, things (mostly) make sense now.
Also, starting from Category:RuPaul's Drag Race, you can browse through the categories and pages and find (pretty much) any page or sub-category fairly easily, and without confusing mis-named categories or pages missing from categories. ...mostly.
So, as far as I'm concerned, I'm calling the categories wrapped up.... for now. There are probably lots more categories the queens could be tagged in, but that doesn't affect the "doneness" of existing categories. :P
The only thing I think might be confusing.... There is a Category:Queens where queens get divided into sub-categories (by season or other commonalities), and then there is Category:Queen, where every individual queen is (the page total for that category is exactly 100). I thought it was a nice way to do things, and since both categories already existed before I started cleaning up, I figured it would be easy enough to keep them separate and functionally different.
ANYWAY... cleanup up, browsable, and uniform. I'm calling the category cleanup task done.