Jailbreaking requires less technical skill than you might think. There are easy-to-use jailbreaking apps and stores of apps that can be used on a jailbroken device.
But is it legal? Yes and no.

Late last week, the Librarian of Congress issued the latest set of exemptions to a copyright law that covers this kind of thing, the Digital Millennium Copyright Act (DMCA). It said that smartphones were exempt and that tablets were not. 

In other words, if you jailbreak your iPhone you can't be sued for DMCA violations. But if you jailbreak your iPad, you can, even though you would be running the same jailbreaking app on the same operating system, just on a larger device.

Go figure.