Sasuke could be one. He's highly intelligent and has his own network of contacts. He might introduce Naruto to some high - paying jobs or business opportunities. Another one is Tsunade. As the Hokage, she has access to a lot of resources and information. She could give Naruto some inside tips on how to make money, like which trade routes are the most profitable or where to find rare and valuable items.
Jiraiya might also play a role. He travels a lot and knows about different cultures and their valuable assets. He could help Naruto discover some unique items or knowledge that can be turned into wealth. Also, Shikamaru, with his brilliant mind, could come up with smart business strategies for Naruto. He could analyze the market trends in the ninja world and guide Naruto on which businesses to invest in.
Iruka sensei could also be very helpful. He has always been like a father figure to Naruto. He would support Naruto through this strange transformation, offering advice on how to handle the reactions of others in the village and how to adapt to this new situation without losing sight of his ninja goals.
Iruka could be a surprising character to abandon Naruto in some fanfictions. Maybe he gets influenced by some outside force or a misunderstanding that makes him think Naruto is no longer the Naruto he knew. And then there are the other genin in Naruto's class. They might abandon him out of jealousy if Naruto starts showing extraordinary powers too quickly. Or they could be pressured by their families who don't want them associated with Naruto.
Iruka - sensei would be very likely to help. He was Naruto's first teacher and has always cared about him. He could use his teaching skills to reteach Naruto things he's forgotten. Hinata would also be there for Naruto. Her love for Naruto is strong, and she would do anything to help him. She might use her Byakugan to look for any physical problems in Naruto's body that could be related to his memory loss. And of course, Jiraiya. If he were still alive in the fanfiction, he'd be a great help. He trained Naruto and knows him well, so he could use his sage knowledge to assist in getting Naruto's memory back.
Often, in these fanfictions, Naruto gets rich through his connections. He has made friends with many powerful people during his adventures. Some of these friends might offer him lucrative business deals. For instance, he could partner with a wealthy merchant from a neighboring village. Or perhaps he creates a new form of ninja training that becomes so popular that people from all over pay large sums of money to participate.
Iruka sensei might also be involved. He has always been like a father figure to Naruto. He could give Naruto the confidence he needs and maybe even help him plan the location for the proposal, perhaps a place that has sentimental value for both Naruto and Hinata related to Naruto's early days at the academy.
Iron Man is another candidate. Tony Stark's technology and Naruto's ninja techniques could be a great contrast. They could learn from each other. Stark might be interested in Naruto's chakra - based powers and try to replicate them in some way, while Naruto could be amazed by Stark's high - tech gadgets.
Naruto, Sasuke, and Sakura are the most obvious choices. They are the main characters and their interactions are always interesting. Naruto would bring his energetic and fun - loving nature, Sasuke his brooding intensity, and Sakura her intelligence and strong - willed personality.
Naruto himself could be in jail fanfiction. Maybe he was framed for a crime he didn't commit and has to prove his innocence from within the prison. Sasuke is also a likely candidate. His brooding and sometimes anti - social nature could lead to him getting into trouble with the law in a fanfiction setting. Another one could be Orochimaru. Given his history of unethical experiments, it's not hard to imagine him ending up in jail in a fan - created scenario.
Obviously, Naruto will be one of the main characters. Since it's about his super luck, he's at the center of it. Sasuke might also be a main character as he often has interactions with Naruto. Their relationship could be affected by Naruto's newfound luck, whether it be through envy or cooperation. Sakura could also be a main character as she is part of Team 7 and Naruto's luck might influence the dynamics within the team.
Definitely the Teen Titans. Robin would be interested in Naruto's strategic mind and combat skills. Starfire might be fascinated by Naruto's unique culture. Beast Boy and Naruto could bond over their fun - loving natures. And Cyborg would be intrigued by Naruto's chakra - based abilities compared to his technological ones.