Somebody asked a question earlier that’s somewhat similar to this. Scroll to the bottom of Youtube and click the “Report a Bug” link. Google’s Feedback Tool (Javascript driven), essentially does what you described. Judging by what I looked at of its code, it uses canvas and has a JavaScript-based JPEG encoder which builds a JPG image to send off to Google.
It would definitely be a lot of work, but I’m sure you could accomplish something similar.