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.
This is only loosely related to your post but I just came across this project:
https://archipelago.gg/
It supports a whole shitload of games: https://archipelago.gg/games
I only just started reading about it. So far it seems like insanity.