I would imagine, even if most users can't do it themselves, other family members or friends will do it for them, in the same way they've been installing Chrome on their computers before. This can quickly (a few years) lead to a large portion of the users using jailkbroken devices, and getting used to having their device jailbroken.
If you are willing to help lots of nontechnical people jailbreak their phones you better have a lot of time for the thousands of support questions they flood you with.
I'm pretty tech savvy, I work with very tech savvy people. Many of them write firmware, network routing systems, and spend hours a day JTAGing various spins of our NICs.
I don't know how to jailbreak my phone, nor have my dozen or so google searches yielded anything useful, nor do any of my colleagues have jailbroken phones - despite being precisely the type of people who want to.
Jail breaking used to be straightforward a couple years ago, but for anyone with a recent phone (I have an iPhone 5, colleagues have iPhone 4S's) - it's become pretty difficult.
I doubt that most of the people who pirate have a recent phone: they probably have hand-me-downs from their parents or purchased the device second-hand off of eBay.
In fact, if you consider piracy a feature, you probably purposely purchase an older phone: Apple still sells the iPhone 4, which continues to be trivial to jailbreak.
