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It boggles my mind that someone would buy a closed source device and wait for it to be jailbroken with each OS update they download. Just buy an Android device.
One could argue that iOS, while "closed" is a more refine user experience, but for some who want to be able to tweak some things that Apple doesn't allow - jailbreak gives them. They get to strike the balance between a solid user experience and the flexibility of configurability. Not to mention the "feeling cool" factor that seems to fuel my friends and coworkers who jailbreak their devices.