Mac stuck on "The wine configuration in /user/... is being updated"
Found this question on Super User:

https://superuser.com/questions/1318059/wineboot-hangs-and-does-not-complete

According to the answer it is a known bug with the Homebrew version:

https://github.com/Homebrew/homebrew-core/issues/26384

The workaround is to use the official version:

https://dl.winehq.org/wine-builds/macosx/download.html