> Is there a possibility of ...automating, this kind of automating?

Nah - I'm going to be cocky for a second so please take this with a grain of salt... Automation is the only job that's safe from automation ;)

That being said, it's prime for development of tools... I've been working on taking a lot of my workflow out of Charles Proxy and moving it onto a more "man-in-the middle" model that can replay certain web traffic... PARTS of what I do, but automating the automating is probably the most difficult problem that I've had to solve (ie: building my own tools).