https://bugs.winehq.org/show_bug.cgi?id=45461
--- Comment #3 from Tobias (:Tobbi) Markus tobbi.bugs@googlemail.com --- (In reply to Ken Thomases from comment #2)
From the app's description, it doesn't provide an on-screen keyboard; it just configures the on-screen keyboard app that comes built-in with Windows. Wine does not provide a similar on-screen keyboard app. I suspect the program is trying to launch that built-in on-screen keyboard, but it isn't there, so nothing happens.
In theory, Wine could provide such an app, but it wouldn't be as good as the one that macOS provides. First, enable System Preferences > Keyboard > Keyboard tab > "Show keyboard and emoji viewers in menu bar". Then, from the icon toward the right end of the menu bar, select Show Keyboard Viewer.
Oh, alright! I guess this ticket can be closed then?