first off, I'd probably have the other character's fully evolved their pokemon. I find it weird how dawn's had her piplup since twinleaf town and it hadn't even evolved into prinplup, let alone empoleon. o.o
otherwise:
Character's Name: ash
Gen I Pokemon: machamp, rapidash, kingler, pinsir, kabutops
Gen II Pokemon: slowking, octillery, mantine, hitmontop
Gen III Pokemon: shiftry, pelipper, medicham, flygon
Gen IV Pokemon: luxray, bronzong, rotom
Gen V Pokemon: sawk, carracosta, reuniclus, mienshao, braviary
Character's Name: dawn
Gen I Pokemon: charizard, sandslash, exeggutor, vaporeon
Gen II Pokemon: ledian, xatu, ampharos, dunsparce, kingdra
Gen III Pokemon: sceptile, mawile, manectric, altaria
Gen IV Pokemon: drifblim
Gen V Pokemon: samurott, zebstrika, whimsicott, gothitelle, swanna, galvantula
can't be bothered doing any more characters, but those just come up off the top of my head.
Nice suggestions, I was picking some of those too.
Here's what I think:
Iris
Gen I Pokemon: Lapras, Vileplume, Dragonite
Gen II Pokemon: Kingdra, Ampharos, Umbreon
Gen III Pokemon: Sceptile, Altaria, Camerupt
Gen IV Pokemon: Garchomp, Mismagius, Purugly, Honchkrow
Gen V Pokemon: Hydreigon, Emboar, Zoroark, Simisear
Misty
Gen I Pokemon: Blastoise, Vaporeon
Gen II Pokemon: Quagsire, Azumarill
Gen III Pokemon: Swampert, Milotic
Gen IV Pokemon: Lumineon, Floatzel
Gen V Pokemon: Jellicent, Samurott, Simipour
Dawn
Gen I Pokemon: Golduck, Butterfree
Gen II Pokemon: Miltank, Xatu, Granbull
Gen III Pokemon: Manectric, Grumpig, Spinda
Gen IV Pokemon: Skuntank, Froslass, Roserade, Ambipom (she might get another one cos she gave an Ambipom to O)
Gen V Pokemon: Gothitelle, Beheeyem, Beartic, Zebstrika
May
Gen I Pokemon: Hypno, Snorlax
Gen II Pokemon: Bellossom, Blissey, Lanturn
Gen III Pokemon: Plusle, Minun, Flygon
Gen IV Pokemon: Lickilicky, Yanmega
Gen V Pokemon: Simisage, Reuniclus, Swanna, Liepard
