Signing Differently as One Recipient

I do not believe that is possible.  When you have a single Recipient with “2” Signature blocks and you send that envelope the Recipient clicks the first Signature block and adds the Signature, then if they click the second Signature block it adopts the first Signature.  Now if you try to “change” the Signature of either block there is a popup that tells you changing one will auto-update the other Signature block.  Basically the Signature blocks for the Recipient must be the same when multiple fields are applied to that Recipient in the case of Signature blocks. So I see your only solution as sending the envelope to the same person multiple times with slight differences in the Recipient Name.