I do this all the time too, but I think you're wrong about the ssh difference.
ssh doesn't see the keystroke until it's fully formed by your OS and/or window manager, so there can be no latency to the release of shift.
ssh doesn't see the keystroke until it's fully formed by your OS and/or window manager, so there can be no latency to the release of shift.
It predicts what the server will do with your input and displays the result (with an underline) until the server responds. This means typing is always at local speed even if the network is being flaky.