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0e1f616
(Get the code!)
My 2 cents:
For server, there are lots of other places where password behaves the same (including login) so for consistency I wouldn't change sudo behavior.
For desktop, in most places, privileged actions trigger a GUI pop-up in which you enter your password (with the "usual" password feedback). If I use run ssh client on a server, I have to enter my passphrase at the terminal prompt. If I do the same on a desktop, I get a neat pop-up in which I can type my passphrase. I think sudo should ideally behave the same...
I didn't look into feasibility at all here, and I assume if it was that easy it would already have been done. I just don't think we should have a different "sudo" behavior *in terminal* based on an abstract detection of desktop/server. I think sudo could on X-enabled systems ask for its password in a different way.