I have a question because I've never bought anything on itch.io, if I buy the game now, when another update comes out will I have to buy it again?
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If you spend the $5, you'll get every future version valued at that amount or under. That's how itch.io handles donation-based financial support... honestly, I think it's confusing. I don't plan to increase the values on anything until the game is 'finished', so you'll be getting version updates for the foreseeable future.