That’s what I was wondering- was if it was connected to an issue with the code itself and not so much the hardware of my server.
I guess my next possibility is just writing my own plugin with a script to manually update myself.
Glad others have the same issue so it isn’t just me (I know it sucks). Maybe someone who develops actively with Discourse can check into it. I also wish there was better debugging info more so than it just “fails”.