I think the Deerling to Sawsbuck would happen on the beach in Moon Country. It’s pretty late, yeah, but it’s also a very solid moment of moving from a child’s innocent success in missions to an adult’s grim cost to success.

Hmm… thematically that’s a good choice–since, as you said, that is the first time she summons Heijomaru in a combat setting–but I’m just… Her Deerling is her first Pokemon, so that seems awfully late.

Then again, Ash’s Pikachu is never going to be a Raichu and it’s been how many years?

Then again, again, Raichu needs a Thunderstone so Pikachu can just avoid that, whereas Sawsbuck are only a level 34 cap so…

Unless that’s where Shikamaru’s Deerling evolves?

I feel like, between the twins, Shikamaru probably wouldn’t use his Deerling as much in battle so maybe Shikako’s Deerling evolved earlier (the equivalent of when she would’ve signed the summon scroll).

Ugh, I dunno. I also don’t know how I would translate certain fights into Pokemon battles which is why I kept everything vague.