Sudeko (or Samara) can't be killed, so she would get them eventually. Then again, if you destroyed all the tapes, or Pinhead warped into her dimension...
When do you actually see the devil's face? Pyramid head isn't a boss, he's not even real, and sometimes there's more than one: so no, despite how cool he is, no. Freedy isn't Itachi, wtf.
Sadako would destroy everyone. Samara is weaker than Sadako, but she'd still destroy everyone. Next up is probably Freddy. Weakest is leatherhead, why is he even here? He's just part of an insane family TCM bestiary.
chucky's face and the way he moved around always scared the living crap out of me is it uncanny valley related since he was animatronic? i dont know....