Thanks for the info. Really appreciate it.
I was going to look into PICs like PIC16F628A as the cost is very appealing but I knew the stamp would be easy to work with from the get go as this is my first electronics project ever (Short of blinking an LED when I got the stamp). :)
But if I do a version 2.0 I will try that PIC out. I looked into etching a board for this but seemed like too much hassle but I did give Eagle a go for circuit design I will checkout KiCAD. I got my part this morning that converts the iphone port 3.3v to 5.5 so power is not an issue.
Olimex seem really cool. If I bump into a passionate iphone owning money man and an interested electronics engineer I will be off. :)