The perv only wants to look at the half-naked ladies. I doubt he would be concerned about teaching some shinobi that fights him. How about you just pull a Naruto and pester him to death until he trains ya.\
"Geez kid, I only wanted to look at the ladies for my umm... reasearch!" says the pervert. You notice how much of a battle he was, and immediately ask him to train you. He says no, but you aren't going to give up without a fight. The perv sees you getting your weapon ready and knows that you will fight him till the end until he trains you, so he finally gives in.
Anyway, the dating part... just has to be taken out. It's too much of a date simulator/just weird. Also, the perv(lets just admit it is Jiraiya) wouldn't let some Shiniobi he lost to pick out a date for him.
Also, fighting his student, don't believe that would work, Naruto doesn't really care as long as he gets his ramen. XD
15 chakra(points?)... is just way too much, would never be accepted. 15 chakra points, is what the leveling is for. Alongside that, summoning jutsu, you have to figure out a way to get it to fit with the other jutsus and it would just be like having two mounts, and we don't want it that easy.
Also, the perv is too nice to someone who disturbed his looking at half-naked ladies.
*exhales* there ya go... This event is also very very similar to the Ero-Sennin event, and we don't want to overwrite that very nice event.