See, as things stand at present, Apple plays cat and mouse games with both the hackers behind the jailbreak projects and those who have jailbroken their handsets, with firmware updates traditionally destroying any jailbreak. But now that jailbreaking has been given a legal seal of approval, will Apple change it view of jailbreaking and jailbreakers.
We already know that Apple won't offer support for any damage caused through jailbreaking, which I guess if fair since it's making the product do something that it's not designed to do. But even with that point clarified, it still leaves many other questions:
- Will Apple continue in its policy of making jailbreaking progressively harder with each update?
- Will Apple continue to build updates in such a way that undoes existing jailbreaks?
- Will Apple offer an easier way for iPhone owners to jailbreak?
- Will Apple now loosen up API restrictions of developers to allow them to add currently prohibited functionality to apps (one of the primary reasons people jailbreak - other than pirated apps - is to get access to apps that provide features that wouldn't be allowed by Apple).
My prediction is that Apple won't make life easier for jailbreakers unless there turns out to be some sort of legal challenge to updates undoing a jailbreak. Until that happens, jailbreaking is going to be a) for the technical b) not something that the mainstream user will be interested in.