Re: career outfits stopped working
@LieutenantGuac This seems like an uncommon but not unheard of issue with NPC career outfits. As far as I can tell, there's no perfect solution, or even a definitive cause. You mention you use mods, although not which ones, but I'm guessing your list includes a few entries from NRaas. One thing I have seen mentioned is the StoryProgression setting to force sims into everyday clothing. To see the setting, click on City Hall and select NRaas > SP > General Options > Options: Careers > Force Change Work Clothes. Having this on True may be affecting the NPCs' outfits even when they're technically working.
If you do change this setting, a MasterController reset on the affected sims is in order as well. (From City Hall if the NPC isn't on screen: NRaas > MC > Sim > Advanced > Reset Sim.) You could also try a DebugEnabler "fix invisible sims" command, which is supposed to fix any broken outfit assignments. On City Hall, I believe it's just NRaas > DE > Fix invisible sims.
But this issue can be stubborn. I don't use StoryProgression myself, and I recently saw a French newspaper deliverer show up in a blue suit, which didn't seem like the right answer. A different one in Egypt was missing her top entirely though (she was a floating head and legs), so there might be a larger issue in my game. If you get really frustrated, you can always use MC to copy an NPC's career outfit to their everyday outfit as well, so at least they look normal.