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I apologize if this is an uninformed question, I am not 100% familiar with how itch.io works, and downloading games, if I have data from a previous version, is it possible to import it to a new version? or if I have all my files from both versions in the same place will it keep track of my old save data? 

I guess this is on PC. If you use the itch laucher, the game will automatically update and read your saved games.

Otherwise, you can download the new version and it will read your old games anyway.