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Wine weirdness

I am in the process of switching to Linux Mint (an Ubuntu derivative), after over a year of frustration with Windows 10. As I've been using Take Command and its predecessors for 30 years, I have numerous tools and batch files that rely on it, notably the ones I use to build my Web site. I expect to eventually master shell scripts, Python, and C++ and translate everything, but that will take a while. I still have a dual boot into Windows 10 to run Photoshop and Finale, and also to build Web site updates in Take Command. But I'd really prefer to avoid booting into Windows for the latter. (The latest version of Finale runs decently with wine, so once I upgraded I no longer needed Windows for that.)

I successfully installed Take Command 24 with wine 6.0. The first weird problem is that TCC launches only 25% of the time. When it does launch, it works correctly as far as I can tell. But when it doesn't I either see a blank console window with no text or cursor, or the console window comes up and immediately disappears. Take Command always seems to launch and run correctly, including the File Explorer, ribbons, and options. But the TCC windows behave the same way as launching them directly. I meed to open new tabs until I get one that works, typically 25% of the time.

This makes no sense to me, as an application should either be compatible and run all the time, or incompatible and never run. There's nothing I do differently when it does run, and there's no pattern I can discern. Sometimes TCC will work on the first attempt, or Take Command will launch with a functioning TCC window. Other times it will take eight attempts.

The second weird thing is even stranger. When I get TCC running in a Take Command tab, the shift key doesn't work. It's not possible to type uppercase letters or special characters. The keyboard works properly in the Command Input window, which provides a workaround. It apparently works everywhere else in Take Command. It also works when I'm running TCC without Take Command. Very strange.

Any ideas, suggestions, or workarounds?