>>57306700Start: Lass Serena (if you're male), Youngster Winston (if you're female)
500 wins: Other supporting player character (Dawn/Lucas/Lyra/Ethan)
1000 wins: Mom (Johanna/Johto mom)
10000 wins: Professor Oak + Jasmine (Platinum)/Whitney (HGSS)
As you use different Pokémon, Serena/Winston's dialogue updates at fixed intervals to show greater and greater admiration. Once you've used all 475 Pokémon allowed in the Battle Hall, they're basically simping for you.
Beating the post-game League in Platinum 20 times upgrades Barry's post-game team by 20 levels, he was the first non-Battle facility Trainer to use Pokémon above GSC Red. He also has another team that's only 10 levels above his normal post-game team, and the condition mentioned in guidebooks was that you had to beat the League 10 times to face it, but apparently the condition was never properly implemented so you can't battle this mid-updated team.
