As useful as the Pencil is, there are a few drawbacks: although it comes with its own case, there's no built-in storage on the iPad Pro itself, so you'll have to carry around two separate pieces of equipment. We're guessing that third-party Pro cases will solve that issue sooner than later (surprisingly, the new Smart Keyboard doesn't include any Pencil support either), and you'll certainly want some protection for your investment, so you'll need a case anyway. And the $99 price tag, may be a little steep for some.
As for Steve Job's famous "hatred" of styluses? At the time when Jobs made his now infamous comment, styluses were used more as fallback for touch-screens that weren't sensitive enough to work well with fingers. With today's touchscreen advancements, the Apple Pencil can add another dimension of use for artists, designers, and hobbyists looking for some extra touch. This is something Jobs didn't take into consideration before, because he didn't need to.