Women do play a significant role in a man's life and how he shapes up. Jiraiya couldnt bear his close friend betray his comrades and also couldnt bring himself to get acquainted with Tsunade. His bond with Tsunade is similar to Naruto's bond with Sakura (coz Tsunade preferred orochimaru to Jiraiya for a date. Jiraiya couldnt save his friend Orochimaru from Darkness. He cursed himself by imposing a self exile to have a watch on him. His regret is evident when he rejected the offer of becoming the HOKAGE. Naruto is shaping up like Jiraiya and resembles his Mentor in many ways. His words "I AM NOT WORTH BEING A HOKAGE, IF I AM NOT ABLE TO SAVE MY FRIEND", is just an example. Look how Sakura is shaping up Naruto.
Jiraiya is named after the character of the same name from a Japanese folklore "The Tale of the Gallant Jiraiya" (Jiraiya Goketsu Monogatari). The Jiraiya in this story excelled in summoning a giant toad (the toad itself was sometimes called "Jiraiya") and toad magic. In that story, Jiraiya and Tsunade were a married couple. There, his name is written as "Young Thunder", which in turn comes from the name Garaiya ;( Literally meaning "I came") from the Chinese story Kaishi . As the character was about to die, he made a reference to the story.
Masashi Kishimoto originally planned to draw Jiraiya with a different design, and with a different style of hair. He also intended for Jiraiya to summon toads that were of a similar size to humans. However, this idea was deemed a failure. During an interview, he commented that, of the student-teacher relationships in Naruto, Jiraiya and Naruto's is the one he likes the most.
The Three Legendary Sannins
The Sannin (Densetsu no Sannin; Literally meaning "Legendary Three Ninja") were the students of Hiruzen Sarutobi, members of his Team Hiruzen: Jiraiya, Orochimaru, and Tsunade. They possess exemplary ninja abilities. When they were young and relatively unknown during the Second Great Shinobi World War they fought against Hanzō, and for being able to survive his attacks he gave them the title of Konoha's Sannin in return for letting them live. After that, their names became famous throughout the world.
The Sannin are widely regarded for their great skill and power, each one has the level of being a Kage in their own right; each has been considered for the position of Hokage at different points in time, with one of them obtaining the title. When Orochimaru defected from Konoha after being denied the position, the Sannin were disbanded, though they continued to be known by the title. As time passed, Orochimaru and Jiraiya died, and Tsunade is in a coma.
Inititally as graduated from tha academy as a GENIN Jiraiya was under the then Jounin Hiruzen Sarutobi, who eventually became the sandaime Hokage. Sarutobi had Jiraiya, Tsunade and Orocimaru as students. The first test for them was the bell test, which Jiraiya didnt fare well.
Jiraiya is one of the legendary sannin's who died for the sake of the NINJA world. The person who was overtold a prophecy that He will, in the future have a student who will have the power either to bring order or bring chaos, and he would have to take a critical decision that would eventually influence the prophecy. As overtold he did have, but there were two of them Nagato and Naruto. He made the choice, he wished Naruto would fulfill the prophecy.