I have to say that what I find really off putting about "Pressy" is the idea of having to constantly unplug it and replug it back in when I am using headphones. I would definitely lose it within a month after plugging in my headphones, putting it down on my desk, and it disappearing under papers.
That's precisely the kind of thing these crowdfunding projects seem to miss. It's always the tiny things which turn out to be annoying and make the project less 'amazing' than the video would suggest. Like I sponsored a Kickstarter project for a keychain Android Sensor, and the designers failed to install an on-off switch, with the result that it runs out of juice in a couple of days. It's almost unusable because of that (who wants to keep plugging their keychain into a USB charger every night?)