I bother for two main reasons. Firstly, I vastly prefer the hardware of iOS devices over the competitors. Secondly, the software openness isn't that big of a deal—I still prefer stock (non-jailbroken) iOS to stock Android (I confess that I haven't extensively tried Windows RT or any other alternatives).

Jailbroken iOS is just icing on the cake. When there's a major iOS upgrade that causes me to lose my jailbreak, I lose a few niceties (the biggest of which is the ability to "try," as in pirate, applications), but it's not a big deal.