I think you're right about it being a mostly automated process right now -- but don't think making them doing a little work will scare away the pirates. I bet there are lots of kids in the iPhone warez scene looking for a challenge.

I did some research into mobile app piracy 3 or 4 years ago and found a thriving scene for cracking WinMo, Palm, and J2ME apps and games. And these were not automated cracks, someone sat there with a debugger and reverse engineered the registration keys.