> .then waiting until I typed a pin and stealing my phone again seems like a bit of a hassle.

Why would you have to steal it again?

> Or, do they have to jail break my phone to do it?

They will most likely have to jailbreak it.

> I just don't worry about things and shit seems to work out.

Yeah, sure, nobody ever said it happens often, it's for the time it happens that it save you so much trouble.

A friend got his credit card stolen recently, no big deal, I'm in Canada and the bank take all the blame in theses cases. It still was way too much trouble to get a new card because the guy changed his card information and the bank couldn't validate his identity.

It's not always about what you may lose, it's about what may happens to get back from it.

> It's just stuff. Perhaps if someone stole everything from me, I'd be even more free than I am now.

I don't believe you, but good for you if believe it yourself.