EDIT: Setting graphics to max fixes the issue somewhat; the correct hair shows up on the same, but the portrait hairstyle still has the original incorrect with the bald spot.
Did you neglect to clear your caches, by chance?
Oops...doing that now.
Sometimes you have to wait for the portrait to update.
Thanks for all your help!
By the way, I posted the same question to modthesims, and this was their response:
All hairs have four different meshes. The first mesh, LOD0, is used in CAS, and in-game if you're zoomed right in and have a very good graphics card. The other three meshes are used in-game if you zoom out a bit, or if your graphics card isn't great. With that hair, Skysims didn't bother making the three ingame meshes, just the CAS mesh; which is why the random EA hair (the hair Skysims used as a base) shows up in-game. That's taking pride in your work, alright.
So I'm wondering whether or not the bottom, side, and wheel interaction portraits use the other meshes, since they don't update when I max my graphics settings