That's very strange... There's also the option of using the data disk mode and uploading the game directly. Instructions are found here: https://help.play.date/games/sideloading/. Let me know if you're still having issues.
I've also went ahead and submitted a request to itch io support to refund the duplicate purchase.
Thank you!!! I got it working last night through the data disk mode and this morning after an update it works like a charm. Thank you again Squid God for the help and I'll swear off Calamari in your honor! Cheers from a fellow Dev (Niantic Artist).
p.s.
Really wish the PlayDate had a backlight, would love to play your games in the evening lol.
