He did and didnt care
the Naruto in the series was selfless almost too selfless he was willing to sacrafice everything for Sasuke. and that is the major issue, he had no concept of the long term effects of his actions and was all about immediate gratification
if he didnt gert Sasuike back then and there he was a failure
if he didnt gert Sakura on a date he failed
basically he let himsefl become a legacy of immediate failures which he had to be pulled out of and set back on couse by others reminding him to keep on trucking. the problem with this was while he did care about people he would get so caught up in his immediate goal of this or that, that he would tunnel vision on said goal forgetting that other people and things exsisted
Yeah - it would have been interesting to have Jiraiya come back and connect with Naruto on letting go of your old teammateand moving on.
After all, Jiraiya is supposed to have left the village and turned down the Kage position (which the Third was wanted him to take) so that he could follow Orochimaru around and either a) try to make him see the light, or b) stop him from harming others. Well, Jiraiya failed on both counts didn't he? Cause he didn't ever change - in fact he only got worse and started capturing and locking people up for medical experiments, and got so big he apparently formed his own country (Sound). And he harmed others in a massive way — including coming back, attacking the village, killing the Sandaime (his former teacher) and the leaders of Sand, as well as scores of other nins.
Jiraiya failed in bringing Orochimaru back, and he failed in protecting the ones he loved. And Orochimaru went on to 'poison' Sasuke and make him defect the village, causing the whole cycle to continue.
I know he's dead...but that apparently never stopped anyone in the Narutoverse from coming back!! So it would be interesting to see Jiraiya come back and say "You know, if I had just killed Orochimaru way back when...then AAAALLLLLLL these people would still be alive...."
Instead, we get to see Naruto paying the price for Jiraiya's mistakes, and reliving the whole cycle! Ugh!