I use to love digging deep into all of my gadgets and tweaking every possible setting until it was perfect for me. It was cool to have something perfectly customized to my every whim, and it was neat just to try out new ways of doing everything.
However, over the years I got tired of having to spend copious amounts of time learning how to tweak new systems, figuring out which new tweaks I needed or wanted, and dealing with the problems that can pop up when rooting a system.
I don't doubt there are benefits to jailbreaking my iPhone, but I don't see these benefits as outweighing the simplicity and ease of using the phone right out of the box. I can purchase a new phone, run through the activation, and set it up via iCloud in maybe 10 or 15 minutes. I know I can't possibly jailbreak, sift through all the apps, and get it set up ready to use in that amount of time.