Assuming that both questions regard replacing Kim, unless it's known to the audience that Carol is a male (unusual, but not unknown), then "With whom does Kim think that Carol hopes that Jim says that her coworkers would like management to replace her?" is ambiguous, and violates the grammar rules I was taught. Because the antecedent of the pronoun is not the nearest appropriately-gendered noun, one must replace "her" with "Kim" to be painfully correct.