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.

-- 
Entering password in Terminal gives no visual feedback
https://bugs.launchpad.net/bugs/194472
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