Silktree here. It's a bit of a shame that our alternate timeline theory seems to be wrong. SM following OS would have made more sense than a linear timeline, although Ash's SM personality is even inconsistent with OS. He's dumb outside of battles, whereas in OS he had wit despite lack of experience.
Would you have any interest in joining my Pokémon VS Digimon RP? I see you've already written your own take on the Pokémon/Digimon crossover idea with your Xros World Adventurers story (which, unfortunately, I cannot have the pleasure of reading since my knowledge of Japanese is extremely limited). We just need one more player to get started.