I’ve jailbroken every past iOS and iPhone I’ve had. Except for my iPhone 5S and iOS 7. There are some awesome jailbreak tweaks, and new ones are created every day. But as tempted as I am to jeailbreak, I’m also not tempted.
I think my biggest issue isn’t doing the jailbreak, or dealing with the chance that I’ll have an unstable device. My issue is going through the setup of all the tweaks I’d want to install. I know of several that I know I want to install, but then there are the hundreds and thousands of other apps, tweaks, and mods to sift through.
Last time I used Cydia, it still wasn’t a user friendly store (this may have changed recently). There is no way to sort out the awesome useful tweaks and apps from the shitty ones that only matter to three people because it does something extremely obscure.
I’ll probably end up breaking down and jailbreaking my iPhone. I really do miss some of the better tweaks, especially BiteSMS.