A Screenshot Plugin for my Parents

Standard situation: My wife is on skype with her parents. Something on the other end doesn't work. They discuss for 20 minutes before my wife even knows what the issue is.

What we need is a plugin for pidgin, skype, adium and others that allows someone to take a screenshot with one button. A preview would then pop up and the user could touch (or click on) the region where the issue is. The screenshot would then be sent through and displayed on the other end.

My stepmother would push the button, click on the area of the screenshot and my wife would then see the screenshot with an enlarged set-in.

Alternatively, my wife could hit a button and the screenshot would be requested on my stepmother's machine.

Would be a life saver. Or at least a good time saver.