This challenge will involve Naruto going through the Kanto region first along side Ash or at least at the same time. Naruto will have a similar mindset to Ash in the fact he's not academically smart but is smart mid battle and unlike Ash he will have knowledge about pokemon such as how to treat them what they eat things like that. I did read a fanfiction where he was in the woods and was sage like and I liked the way it was set up in how he interacted with his pokemon and the potential harem. For this story trainers start at age sixteen so they don't die and have some knowledge about what they are doing. Naruto will have received a pokemon before the other trainers as a gift from Oak thinking that it will help temper his personality so he doesn't charge headfirst all the time. His starter will be "don't crucify me" Bulbasaur. Now hear me out Venusaur may seem like the worst choice in a starter for Kanto next to Charizard and Blastoise but its still a pokemon that is good and underestimated. Venosaure is a bit more tanky in a battle of attrition than the other two with things like synthesis, leech seed, rest, plus things like powders mean a clever trainer will be able to use it in different ways then the other two so with someone like Naruto who thinks outside the box Venusaur compliments him the best. True it's far from the fastest but Naruto can catch other mons that will make up for it, besides Venusaur is the best grass type in the first generation. Another reason for giving him a Venosaure at the start is to go with his first harem member Leaf who will be learning from him and watching him through battles and such. Naruto's Kanto Pokemon he has will be (final forms in no order) Venosaure, Dodrio, Primeape, Nidoqueen, Dewgong, Arcanine, Gengar, Sandslash, Golem, Electrode, Kangaskhan, Tentacruel, Jinx. As you can tell there is one for each typing and most if not all of them are the less popular ones for people to choose save Gengar the sole ghost of Kanto the reason for this is simple I like them and want them to be used plus they can go with Naruto in various circumstances such as speed, recovery, unpopularity, or just versatility. The harem for Naruto will be Leaf, Sabrina, Giselle, and Janine. Each of these are for a reason, Leaf is from how a friendship/teacher student relationship can develop sort of like Hinata only less speed up, Sabrina is from how they can bounce of each other and help each other from loneliness and misunderstanding, Janine from the whole being a ninja and getting better from starting at the bottom since in the anime she was just the daughter of a gym leader with a venonat but in the game she got better and actually became the gym leader, Giselle is there for what Naruto's goal in the anime was to be acknowledged and be the greatest however for this she'll see him as a final goal someone who has grown to not care about what others think and can still be grate and not care about if he loses but rather care that his pokemon got hurt.