Gary and Ash in one team, More like the game
A Female Contest and a Breeder for love interest, A Rival
All Three get different starters and Yeah like the games, In a way
Kanto, Johto, Sevii, Hoenn, Battle Frontier, Sinnoh, The other places
Gary's Team
Blastoise
Fearow
Parasect
Gyarados
Eevee (Which he keeps, Evolves to Umbreon)
Arcanine
Satoshi's
Charizard
Pidgeot
Venomoth
Lapras
Rapidash
Eevee (Espeon)
Yeah change their personalities, Well just Ash's
Huh, that would be pretty interesting. Having Ash and Gary journeying together... Think of the possibilities, which you obviously have.
I too would have introduced Contests earlier, and would have liked Jessie to be the main Contest doer in Kanto/OI/Johto. Also, have her be Delia's niece. I don't think I would have her win the Grand Festival in Kanto, and the Orange Islands would be a relfective period for her, and then she would win in Johto.
I would change up the teams some, and not have Brock I don't think. I don't hate Brock, but the Breeders don't particularly have a use, and yeah. He could join Ash later.
Misty would stay, and I would have James join the group. And of course, Meowth as Delia's pet who has to watch over Ash. I know I sound like a TR fanatic, but if the anime was rewriten, I would rather have a darker group of villains the JJ&M, but still keep them. James would be trying to become a Police Officer and competing in challenges to go to the Police version of the League and Festival to attend the police academy of his choice free of charge. He would win and leave the group in the Orange Islands to attend school in Blackthorn. He would rejoin the group sometime in Johto.
Misty would probably have to journey to do something about her Gym. Her sisters would have lost ownership to another person, and Misty would be traveling to win back the Gym. We could see how one goes about becoming a Gym Leader. She would fail at first, after doing certain tasks and then losing a battle against the new Gym Leader, but after a training period in the OI, she would win. I'm not sure if she would go to Johto or not.
Teams -
Ash:
Pikachu
Spearow -> Fearow/ Caterpie -> Metapod -> Butterfree - I can't decide between them. Butterfree for nostalgia. If Fearow, he would have captured the Spearow afterit tried to kill him and Pikachu(like in the real anime). Not Pidgeot, but I'm not sure why.
Charmander -> Charmeleon -> Charizard
Krabby -> Kingler
Bellsprout -> Weepinbell(-> Victreebel?) - Weepinbell, it would be the one James had...
Cubone
Oak'd: Muk, Tauros, and maybe Scyther.
Misty:
Staryu -> Starmie
Seel -> Dewgong
Gyarados
Psyduck
Tentacool -> Tentacruel
Omanyte
Home: Goldeen - Would make a return in the Orange Islands. Misty told it she had to leave it at home where she can swim but will bring it to an island region.
Jessie:
Oddish -> Gloom - First Pokemon.
Ekans -> Arbok
Squirtle -> Wartortle - The one Ash had.
Eevee -> Jolteon
Lickitung
James:
Growlithe -> Arcanine
Koffing -> Weezing
Bulbasaur -> Ivysaur - The one Ash had.
Horsea - The one Misty had.
Ditto
Gary would appear in places akin to Blue in the games and just more often. Damien would appear again after not making it to the league and is destroyed in battle by Charizard. Jessie would have a rival in Cassidy maybe, and James, I have no idea.