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Auto updates only happen if you're playing though the itch.io app (similar to how steam games work).  If you're just downloading the zip, you'll need to download the new one from the itch.io page (your save files will carry over, since they're stored elsewhere, in appdata)

Yes, that worked. Though, do I delete the old application? Since the new app has the files? I'm still working on transferring the mods I downloaded first.

The way the game loads the custom maps is by looking for the custom maps folder that's in the same folder as it's exe (the one it's running from). So if you want to keep your old custom maps, just copy them over to the new folder in your new install. Then you can delete the old ones