Hm… while I am fond of the Lee and Rockruff parallels (and the pun), I actually would rather lean into more of a taijutsu-only equivalent team for him. Meaning only Normal and Fighting types for Lee.
Neji and TenTen would also have Fighting types, but Neji would have a few Psychic types (which parallels the Byakugan sort of an the idea that even though Lee is faster than god, Neji consistently beats him) and TenTen a few steel types.
Now that I think of it some more, I do kind of like Lee having an unevolved Eevee on his team as per @to-someplace-else’s suggestion. Because there’s something very sweet about Lee accepting his Eevee the way it is and not pressuring it into changing itself one way or another. But, of course, if it wants to evolve, he won’t stop it! But what he wants is for it to be happy. (And, also, Green’s Eevee is so powerful. So majestic and fluffy)
Which I guess brings us to the next point with Shikako’s Deerling. And I suppose the problem there is that I’m not sure why the Deerling wouldn’t want to evolve? In comparison to Eevee evolving into a different Type entirely (generally dictated by the trainer and what kind of team they’re trying to form) or a Pikachu evolving into a Raichu which needs a Thunder stone, as far as I can tell Deerling’s evolution into Sawsbuck is just a level cap.
And it’s a natural (or, at least, simple) process for the Deerling line to evolve into Sawsbuck. It’s basically puberty turning from a child into an adult. Whereas Eeveelutions and Pikachu turning into Raichu are more deliberate, like a medical undertaking…
Is there any benefit to preventing a Deerling’s evolution? More specifically, in this world of shinobi-trainers why would Shikako deliberately hamper her Pokemon’s growth with an everstone? She needs to be battle ready, and a Deerling doesn’t have anything over a Sawsbuck–unlike (and I don’t know if this is game canon or just cartoon canon) Pikachu being faster than Raichu.
That’s true… the only Pokemon whose evolution timing I’m set on is when Sasuke’s Pawniard turns into a Bisharp which I vaguely mentally planned out to be around the equivalent of the Sasuke Retrieval arc. Because ~loyalty~ to village and that’s thereabouts when Sasuke decided friendship was more important than vengeance. Like he is a person and not a weapon (and therefore his Pawniard is also not a weapon)
Pawniard evolves into Bisharp at level 52 which actually seems kind of high… Then again, Pawniard is his third Pokemon and the most strictly offense on his team (in comparison to Talonflame, Cubone, and Lunatone) so I suppose it’s not too out there to think maybe he focussed more on levelling up Pawniard in comparison to the others?
At that point in time he would only have had five Pokemon, and his Shinx/Luxio only for a short while so…
In comparison Shikako might be more the kind of trainer to level up her entire team equally instead of focusing on a few. So there could be some hand waving over the discrepancies there.