I started this challenge recently and I found the mccc mod really useful. When you use a mod for larger households, you can't edit their clothing in CAS without losing all but 8 Sims. Mccc lets you edit Sims individually instead of loading the whole household into CAS. That way you can have all your prisoners wear a prisoner's uniform without a problem. Makes the story feel more real. I do have glitches now and then because of the large household, so I have to reset sims sometimes. Sometimes just hitting pause and play again helps to get all Sims moving again.