Just wanted to thank everyone for their input and add some info for posterity's sake;

I stumbled across Silverback about 5 minutes ago and it's what I was looking for to help along testing. It simultaneously records a video of the user and a screencapture, so you can analyze where they're confused, happy, etc.

http://www.silverbackapp.com/

Disclaimer: I have NO connection to this company, just found this useful.