In fanfiction, Jiraiya seeing Naruto as Hokage can be a very emotional moment. It could be a vision Jiraiya has in a story where he's still alive, or perhaps it's a memory in a story set after his death. This often shows Jiraiya's pride in Naruto and his belief in Naruto's potential to lead the village.
One common theme is the passing of the torch. Jiraiya, who was part of the older generation, sees Naruto taking on the leadership role, representing the new era. Another theme is the realization of dreams. Jiraiya always hoped for Naruto's success, and seeing him as Hokage is that dream coming true.
Jiraiya would probably offer some words of wisdom. He has a lot of life experience, so he might tell Naruto that crying is not a sign of weakness but a way to let out pent - up emotions. For example, he could say something like 'Boy, those tears are like the rain that nourishes the seeds of your growth.'
One possible reason could be that Naruto is feeling lonely. Despite having friends, he still has moments when the weight of his past, like being an orphan and ostracized in the village as a child, hits him hard. Jiraiya might see Naruto crying because of these memories resurfacing.
Well, it depends on the specific fanfiction. Some fanfictions might explore alternate storylines where Naruto doesn't become the Hokage at all. Maybe he decides to pursue a different path in life, like focusing on being a teacher or an explorer. However, in a large number of fanfictions, he does achieve his goal of becoming the Hokage because it's such an iconic and desired outcome for fans who want to see his journey to the top in different ways.
Jiraiya might comfort Naruto by sharing his own experiences. He could tell Naruto about the times he faced difficulties and how he overcame them. For example, he might talk about his training with the toads and how he grew stronger through perseverance.
It could be the First Hokage, Hashirama. Naruto would be amazed by his powerful Wood - Style jutsu and his ability to create the village. He could learn about the original ideals behind the Hidden Leaf from Hashirama.
His friends like Sakura and Shikamaru would surely support him. Sakura, with her medical skills, could be an important part of his regime, providing healthcare for the ninjas. Shikamaru, being intelligent, could offer strategic advice. Also, the younger generation of ninjas who have been inspired by Naruto would be his strong supporters, as they believe in his leadership and the new direction he could take the village in.
Sasuke could be an alternative. He has strong ninja skills and a deep understanding of the ninja world. His experiences have made him grow into a very capable person, and his Sharingan gives him an edge in combat and strategic planning.
Perhaps in this fanfiction, Jiraiya discovers that Naruto is going to be the cause of a major catastrophe in the future. He might have seen a prophecy or some sort of sign that convinces him Naruto has to die to prevent this. It could also be that Jiraiya has been misled by false information about Naruto, which makes him think that Naruto has become an evil force that needs to be eliminated.