Wine has some compatibility differences between its versions — I’ve had to downgrade it before because the newer version didn’t work with the app I wanted. So, if you’re ever in the mood to try again, you could check out an older version, and perhaps try launching a simpler app like notepad which is iirc supplied with Wine.

Also, Wine launched from the command line, with the exe as the parameter, usually prints a lot of stuff some of which may say what libraries weren’t found, and winetricks allows installing those libraries easily (if it’s still around, I haven’t done this in a while). Typically something like ‘MS C++ redistributables’ or the .NET framework is necessary.