It's an interesting question, and one that can only be answered by understanding individual morality.
I personally don't steal MP3's anymore. I feel that this has a direct impact on the people making the music. Would i go to a music show for someone that i liked and steal their physical CD? no, i wouldn't. If i like someone well enough to listen to them i buy their stuff.
Movies are different for me, since stealing from that industry is not really stealing from an individual. Plus, while i may watch their movies, i'm happy to
not financially support them. I think our culture would be a better place without dumb movies. Though they sure are entertaining to watch.
As for distributing leaked doctors, or distributing custom doctors, i guess my question is why? Take 2.1 as an example. Say that someone created custom doctors for the Verizon Pre+ and distributed that. Is that really any better than the script process? I guess i don't understand what this would really gain anyone... Maybe skype on any legacy device? Doubtful, since that is a Verizon specific thing.
Also, since webOS doesn't require "rooting", i think this reduces the need for illegal files. We can overclock to our hearts content without running into legal issues.
As for the iPhone, yes, that definitely breaks the license for iOS. I personally like Apple's approach with it, though, which is to break the jailbreaks with each subsequent iOS release. It makes their software more secure, so they're benefiting from it in some ways.