In Apple's case
Apple is making things worse. Android is somewhat "hacker friendly", but Apple will aggressively issue updates to close up the holes that the guys are using to jailbreak. Jailbreaking an iPhone is a much more complicated process than rooting an Android phone. You have to be careful to save certain things so that your phone can be authenticated through iTunes. Even iTunes itself is becoming a problem. You need to save an older version of it. I cannot upgrade to iOS 5 without losing my jailbreak and some things are no longer working because I am not on iOS 5.
It's become a royal pain in the butt. I'm not working right now due to an accident and I'm playing with things like this to keep myself occupied. If I had a job, I wouldn't have time for it.
My point is, I bought and paid for that phone. As long as I am not doing something that is interfering with my service provider's network, I should be able to do what I want with my own property.
