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.
I’d just count calories and reduce the amount per day until you’re losing weight.
The time of day you eat things shouldn’t really matter. This will also teach you really quickly how to feel full on minimal calories. For me I just try to eat something like raw carrots when I want a snack.