I'm using Wine installed on a Chromebook, which for all intents and purposes is a Windows 10 machine

So whenever I try and run the quest installer (quest580.exe), it runs flawlessly until I click install, at which point the program crashes. I'm not sure if this is an issue with Wine or with the installer itself. Can anyone help me with this?

Perhaps this helps:
https://textadventures.co.uk/forum/samples/topic/nwsz5gf0te6qdtfrwzdmga/quest-5-8-working-in-wine