>>53769793I think it's safe to think that May would have appeared again in XY if Kaori would have been fine. It was literally the best chance for her to reappear given the ORAS release. She had a new design to make her reappearance more notorious and the chance to bring Mega Blaziken with her, and the fact she and Serena appeared to have developed a friendship offscreen in Journeys honestly looks like a what could have been scenario. They didn't have a better chance than that. It's honestly sad that May was the only of Ash's main female friends that never reappeared in Journeys considering how popular she is. We were in the wrong timeline.
Also, off-topic, but I feel that Sawyer could have been retooled into an older Max if the serious would been more consistent with the passage of time. Think about it, a green-themed, smart trainer from Hoenn who greatly admires Ash, chose Treecko as his starter (remember Max really liked Treecko as he mentioned how disappointed he was that his sister picked Torchic instead) and who also has a Slaking (the signature Pokemon of Norman) in his team? Sounds like it could be what Max would be as a trainer.