Oh, how fun! I can't promise it'll stay this way entirely in a year or so, but I tried to base it on aesthetics, usefulness, and / or general preference right now.
Normal: Meowth (not Persian necessarily; Meowth)
Fighting: Lucario
Flying: Staraptor
Poison: Venusaur
Ground: Donphan
Rock: Terrakion
Bug: Scizor
Ghost: Gengar
Steel: Jirachi
Fire: Infernape
Water: Starmie
Grass: Shaymin
Electric: Rotom
Psychic: Latias
Ice: Mamoswine
Dragon: Dragonite
Dark: Tyranitar
Kanto: Starmie (The magic star that kicked your ass and made you love its ability to do so.)
Johto: Tyranitar (Gojira! ...with stone armor and a habit of calling sandstorms.)
Hoenn: Latias (The red dragon... eagle... fluffy... cuter whatchamacall it.)
Sinnoh: Infernape (Power, speed, great offensive types, and one of Ash's best Pokemon ever.)
Unova: Terrakion (Legendary Fighting-types were only conceived NOW? Well, he's got beastly strength and fantastic types to use it with.)
Overall favorite: Infernape (The best Sinnoh starter, the best Fire-type, great designs through his family, and an actually interesting story in the show. And I'm not usually a monkey person.)
Normal: Meowth (not Persian necessarily; Meowth)
Fighting: Lucario
Flying: Staraptor
Poison: Venusaur
Ground: Donphan
Rock: Terrakion
Bug: Scizor
Ghost: Gengar
Steel: Jirachi
Fire: Infernape
Water: Starmie
Grass: Shaymin
Electric: Rotom
Psychic: Latias
Ice: Mamoswine
Dragon: Dragonite
Dark: Tyranitar
Kanto: Starmie (The magic star that kicked your ass and made you love its ability to do so.)
Johto: Tyranitar (Gojira! ...with stone armor and a habit of calling sandstorms.)
Hoenn: Latias (The red dragon... eagle... fluffy... cuter whatchamacall it.)
Sinnoh: Infernape (Power, speed, great offensive types, and one of Ash's best Pokemon ever.)
Unova: Terrakion (Legendary Fighting-types were only conceived NOW? Well, he's got beastly strength and fantastic types to use it with.)
Overall favorite: Infernape (The best Sinnoh starter, the best Fire-type, great designs through his family, and an actually interesting story in the show. And I'm not usually a monkey person.)