I jailbroke my first iPhone, as I had that when there was no App store and I wanted Apps
But now I just leave my iOS devices unjailbroken, as long as the devices works as advertised I don't feel the need to modify it.
For me the tight integration of hardware and software coupled with the fluid and responsive interface make the iPhone feel more Amiga like than the Android devices (which are more like the PCs of the 90s)