Here is what I think.
In my opinion, as more and more people embrace the iPad, more and more people will be unhappy that their iPad is not a PC/Mac. So they will start looking for ways to mix it up and Jailbreaking will likely grow. Yesterday, I showed Blaze to an acquaintance and it drove her nuts. She wanted it. As we talked about what was required, she was quite impressed with iFile. She jailbroke her iPad from our booth at Denny's.
Frankly, I am amazed that the devs of Limerain, Greenpois0n, Redsn0w, JBME and others release their hard work for free. When cash is not involved, people do all manner of amazing things. My fear is we will reach a point where future iterations of the iPad (3,4,5...) will be impossible to JB. Not sure how, but when it becomes a problem for Apple, they will take measures. Then hackers will accept the challenge and we will be jailbroken. Unless Apple makes jailbreaking impossible because of magic hardware.
What say you, F4780y? Can Apple add magic hardware lock mechanisms that make it impossible to JB?
So let me ask the group this: if jailbreaking went mainstream and it became the hot "new" thing to do and legions of users jailbroke their iDevices, what would/could Apple do? I know it is legal and I know the EFF (apparently) wants the LOC to make changes so iPads are specifically mentioned. I expect strong disagreement with my point of view and I am not saying the sky is falling, just wondering if Apple can come out swinging. But the fact is, the ruling everyone quotes does not (specifically) apply to iPads, just iPhones. And yes, if puch comes to shove, courts might also say the rules include iPads. I get the arguments.
I also know we all love our JB and I am guessing tens of thousands of iPad users do not JB because they think it is dangerous and illegal. What happens when it becomes the 'thing to do?'
I am quite confident that an untethered JB will arrive for iOS 5 and any future releases/upgrades will likely be Jailbroken. Very confident about that.