1. Enamored with
    It's, "Enamored OF."
  2. I could care less
    If you could care less, that means you do care. What you're trying to say is, "I could NOT care less." That means there is no smaller amount of caring in the universe of which you are capable
  3. The point is moot
    This is used to mean,"There's no point in discussing the matter," but "moot" means ,"debateable", so maybe the phrase just means that the point is so equivocal, no conclusion can be drawn so just drop it.
  4. The opposite of inside out is outside in
    No, those are the same. The opposite is inside in or outside out