Board Thread:Boruto Discussions/@comment-25319479-20181020083112/@comment-25122992-20181022183130

Well, Obito didn't have much of backstory and buildup when he "died". I mean, he was just a child lost on the battefield without any prominent role for the series' plot except for his Sharingan given to Kakashi, plus the influence on Kakashi's future worldview. On the other hand, Jiraya was a fully formed personality with decades of experience and a significant impact on the plot overall, particularly due to his mentorship with some leading characters of the series (the major figures being Nagato, Minato and Naruto). So it was easier to take an underused Obito out of his noble death persona and give him more character developement (albeit, on an evil path), but it won't be as easy to pull out the same trick with Jiraya whose personality, views and the path of life are too well-known to be bright to suddenly throw them into the darkness.