I believe Jiraiya left the village to seek peace and love that might have turned Oro... And if Oro had changed, Jiraiya'd in the village, 5th Hokage and well alive.... and maybe Oro'd be the 5th...
I think he was just stating it as a possibility since he's someone who has changed slightly so he's saying its a good thing J-man died before he could change any.
I'm pretty sure he means that jiraiya might not have been so driven to prove himself by saving orochimaru and saving the world in his prophecy because those are the things that made him who he is. But he " might " not give up on loving tsunade is what he hinted at.