Jiraiya the Toad Sage (Naruto)

Hard not to see this coming and there's not much questioning what he's gonna do, but there's still some things to be decided.

What village?

Is he gonna have multiple "students" since it's important they learn sex ed?

Does he go immediately for Tsunade or build up to her and make her sweat and become needy or beg him to finally take her?

Is he gonna steal Kushina, get to her first, or "comfort/seduce" her?

Is he gonna go for the girls of Naruto's class? (they'll be 18 so they're fair game)

Is he gonna make his books into the most popular books in the world and people have no reason to be ashamed or ostracized for reading them, even in public?

Is it gonna be the world we know is he gonna custom make one?

This all leaves the two important questions: 1) When is he gonna be? Genin? Before the war? Second Great Ninja war? Jonin Sensei? The Third Shinobi War? Naruto series? Shippuden Series?

2) Is he gonna share the wealth with either his sensei, Minato, and/or Naruto? Personally I'd say no and change it so Kushina is his student and that she's head over heels for him after he saved her from Kumo. Doesn't even have to be a different time to start, but it would be the easiest.