I guess you are refering to Sage mode. Sage or Hermit mode is when someone trained in senjutsu has made Sage chakra (normal chakra mixed with energy from the nature). In sage mode, ninjutsu, genjutsu and taijutsu are stronger, the user becomes stronger and a lot of things. Follow the link for more info.
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Chapter 299 was the first time Naruto went kyuubi.
Naruto Shippuuden does not have "Seasons". It has Sagas (like all Anime series') The Saga in which Naruto defeats Pain is called the "Pain Invasion Arc".
no
He travel to the toad mountains in Naruto Shippuden 154 to learn sage mode
Naruto looks cooler because he master what Jiraiya couldn't. Naruto completely mastered the sage mode but Jiraiya couldn't so he developed some toad features when turned into a sage.