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Sounds like you are playing an out of date beta. Download the latest version from this site.

There hasn't been an update since the last time I downloaded it, at least itch hasn't notified me of such…

I'll give it a go, though, just to be sure.

Redownloaded the game…

… it installed another copy of it instead of updating the already installed copy…

It also doesn't access the same saves as the copy that crashed…

Read the release notes and also the instructions when you downloaded it. 

I think your instructions are backwards, since com.altosandherdone.headmaster seems to be where all my saves currently are, as well as a traceback file.

I'll move them to the non-'com.' location.

Thank you for your help~

The bug must be in the save itself.

But my saves load now, thank you~

You can also just ignore that bug, it only affected day one. The beta worked fairly well it mostly just has more typos.