How Hackintoshing is treated vs how Psystar was treated has proven that if Apple feels a certain hacker community does them little direct harm then they are left alone, and otherwise wrath is swift and brutal.
Jailbreaking seems to be on their ignore list, which means it will probably stay on that list...
I think it's primarily a monetary issue. Psystar was making money from hacking Apple's products and then selling them. The EULA for not putting Apple products on non-Apple products would likely never hold up in court for an individual user, given the American attitude of "I bought it, I own it, I can do whatever I want with it", but they have strong legal grounds to pursue people who sell products that violate the EULA. I think this is why they've had problems attacking EFI-X, since it doesn't directly hack anything - the user has to do it. Kind of like selling people guns and bullets, but since they haven't shot anyone, it's okay. Sorta
I also think it's a marketing issue. People who don't want a Mac might be willing to try Hackintosh, and might get fed up with the flaky operation and buy a real Mac. Grassroots psychology - Apple still has a relatively small userbase, so anything that gets them more exposure is a Good Thing. The same with jailbreaking - yeah, technically Apple is losing money on all those apps, but #1, those people probably wouldn't have purchased the apps anyway, #2, it's more incentive for people to buy Apple's hardware, and Apple makes money off that, #3, which results in more underground advertising for Apple's products because you hear that you can "get free stuff" on Apple's products, and #4, Apple knows that most people are non-technical and will just buy the apps instead of doing the hacking stuff (the app store is much too easy to use vs. hacking for a lot of people). Given their current market cap and cash reserves, I would say their strategy is working pretty well :awe:
I don't entirely believe that Apple's lack of security isn't just part of a larger marketing ploy to boost their userbase over the initial period of time. As far as MP3 players go, I don't even know anybody has an MP3 player that isn't an iPod of some sort anymore. There used to be a mix, but I hardly see non-Apple MP3 players floating around these days.