In my persistence to fit Linux in my life, I’m curious if some “must have” Windows software will work better if I just ran a Windows VM within Linux.
None of the software I need to work is needed to work continuously. They are basically programs that I fire up when needed, for a few minutes, then exited.
Wine will install them, but not run them, so I’m hoping a VM is the answer as I’m not interested in dual-booting to run a few Windows programs occasionally.
Have you checked these all on winehq? It would be nice for them to be reported with logs if they haven’t already.
Garmin Express for example is on there with some discussion here: https://appdb.winehq.org/objectManager.php?sClass=version&iId=40213
It might not help in the short term, but even just having logs for more broken programs could be useful for the wine project.