That depends on how easy it is to do the jailbreak. If you can package a self-contained solution, or provide simple to follow instructions, the word will spread, and a lot of people will be doing it.
When I was buying my Paperwhite, I just ordered the ad-free version from amazon (.com or .co.uk, don't remember which). And then a couple co-workers (agreed, computer people, but very much not the type that's into tinkering or cracking software) looked at me with surprise, because it turns out everyone does the "standard" route - order "special offers" from amazon.de, and save money while getting an ad-free Kindle, because AFAIR initially the special offers didn't even display in Poland, and when they did, apparently everyone knew how to jump some hoops to get rid of them.
When I was buying my Paperwhite, I just ordered the ad-free version from amazon (.com or .co.uk, don't remember which). And then a couple co-workers (agreed, computer people, but very much not the type that's into tinkering or cracking software) looked at me with surprise, because it turns out everyone does the "standard" route - order "special offers" from amazon.de, and save money while getting an ad-free Kindle, because AFAIR initially the special offers didn't even display in Poland, and when they did, apparently everyone knew how to jump some hoops to get rid of them.