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(+1)

No, you don't all you need to do is find the email from itch.io saying when you purchased buckshot roulette and click the link in it to bring up the latest files for the game. (It's explained further here when you try to buy the game and click "I already paid for this...": https://itch.io/docs/buying/already-bought)

(+1)

However, if you want to rebuy it on Steam they don't care if you got it on itch.io or not they won't just give you a free game.