I know that we can place an extended hold when a customer is re-depositing an item that has been returned NSF. What I'm not clear on is can we also place an extended hold when a customer is a depositing a check from someone that they have previously had check returned from? Not the same check, just another they received from the same person.

No - only if the item they are depositing was previously returned unpaid.

If you have doubts, real or imagined, about an item just don't accept it for deposit.

Or have it deposited into a savings account which is exempt from CC.

Or send it for collection.

That's what I would recommend if you have doubts. The depositor doesn't get credit until you receive the funds.