Yea yea fine, whatever, but "to" and "with" do both serve the same purpose, referring back to the "whomever", thereby being repetitive, so one should be removed. It just doesn't sound the same when you say: "It’s probably wise that you explain this caveat whomever you’re sharing this information with."
Should either be:
1. "It’s probably wise that you explain this caveat to whomever you’re sharing this information."
OR
2. "It’s probably wise that you explain this caveat with whomever you’re sharing this information."
Two different meaning actually, but if both are used, wouldn't you say the "with" is just superfluous?