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I > III > V > IV > II
Kanto starters are great. Iconic, powerful, the whole pacakge.
Hoenn comes second. All starters are great, good looking, good in battle, etc, I simply like Kanto ones a little more
Unova third. Samurott is my favorite fully evolved water starter. Serperior looks regal as fuck. Emboar is OK, I'd put him on Infernape tier. Tey hold their own in battle. Serperior is ahrd to use, but it's fun to use something other than "SLAP POWERFUL MOVES. WIN!"
Sinnoh fourth. Torterra is amazing, reminds me of Venusaur, my favorite starter, Infernape is ok, but I don't really dig Empoleon. Still used him, he's ok but not my cup of tea.
Johto last. Contains Meganium, the only starter I refuse to use, and while Feraligatr is great, typhlosion is boring.