Is it pointless? SSH doesn’t send the password out over the wire but instead uses a challenge-response cryptographic system so even if one of the interim machines is compromised, they don’t have access to the clear text password. You shouldn’t be raising passwords (or even passwords in the first place with ssh) but practice defense in depth.

Unless you’re transferring large files the overhead of double encryption on ssh is totally blown away by waiting for human input.

IIRC There’s a fork of SSH that supports not encrypting things if you are trying to transfer large files.