Make sure you report your specific problems. For the stuff that's not used by general population you need to put in some work, but I got a couple of apps fixed through bug reports.
Have a look at the troubleshooting section in the docs https://wiki.winehq.org/FAQ#Troubleshooting for information how to get the logs, then report the issue to their bugtracker. Describe what fails and how and hopefully the logs will be enough to debug it. If they're not, you'll get more detailed questions.
Emsigner (digital signature tool) which is built for income tax only also doesn't work but don't know how I can attempt small fixes.