Naruto would face the challenge of resources. Orochimaru had his own ways of obtaining resources, some of which were unethical. Naruto would need to find legitimate ways to sustain Oto, whether it's through trade, alliances, or new forms of income generation. He also has to deal with potential threats from other ninja villages. They might see Naruto's leadership of Oto as a threat or an unknown variable and could take preemptive actions against Oto.
One of the main challenges Naruto might face is dealing with political intrigue within the village. There could be clans vying for more power and influence, and Naruto would have to balance their demands while keeping the overall peace. Another challenge could be external threats, like neighboring villages that might see Naruto's leadership as a chance to attack. Also, he would need to ensure the economic stability of the village, which includes things like proper resource management and trade relations.
One of the potential allies could be Jiraiya. Even though he has his own ties to Konoha, he might see Naruto's leadership in Oto as a way to bring about a new balance in the ninja world. Also, some of the more open - minded members of Oto itself could become Naruto's allies. They might be impressed by Naruto's leadership skills and his vision for the organization, which could be different from what Orochimaru had in mind.
He might face challenges like maintaining order among the chaotic and often unruly denizens of hell. There could be powerful demons who don't want to follow his leadership, and he has to use his skills and wits to subdue them.
One challenge could be getting the Saints to adapt to his unorthodox methods. Since he comes from a different world with different fighting styles, the Saints might find it hard to follow his lead at first.
One challenge could be adapting to the team's dynamics. Team 8 has its own way of operating, and Naruto is used to his own style with his friends. For instance, they might be more methodical in their planning, while Naruto is more of a 'jump - in - and - figure - it - out' type. So, he'd have to learn to follow their lead sometimes.
One major challenge would be trust. In the underworld, everyone is out for themselves. Naruto, with his trusting nature, would find it hard to know who to rely on. Another challenge would be maintaining his moral compass. The underworld is full of immoral activities, and he'd have to find a way to not get completely corrupted. Also, he'd face constant threats from rival underworld groups who would see him as a threat to their power.
One big challenge would be winning over the trust of the existing Akatsuki members. They have been following a very different ideology, and Naruto's more positive and peace - loving approach would be quite different for them. Also, the ninja world would be very suspicious of Naruto leading such a feared group. He'd have to prove that his leadership is going to change the Akatsuki for the better.
He might face challenges like finding the right place to plant the tree. Konoha has a lot of regulations about what can be planted where. Also, he needs to make sure the tree gets enough water and sunlight. If it's a magical tree, he may not know exactly what it needs to grow well.
One challenge could be controlling the power of the Juubi. It's an incredibly powerful and chaotic force. Naruto would have to struggle to keep it in check so that it doesn't overwhelm him and cause him to lose control. If he loses control, he could end up harming his friends and allies instead of protecting them.
One challenge could be dealing with competitors. If his company is in a competitive field like ninja training, there might be other established companies or individuals who see him as a threat and try to undermine his business.