Seeing the creative ways developers got around Apple's rules, which were even crazier back then, was interesting. I recall downloading HandyLight, a supposed app that lit up your screen in different colours... that was actually a secret mobile hotspot app that allowed wifi tethering before Apple did. Everyone had to scramble to download it in the narrow slice of time between word getting out what it did, and Apple removing it.
I had fun Jailbreaking too and installing Cycorder so I could record video on my iPhone 3g. Good times.