This never-ending problem with CrossOver on a Mac is driving me nuts.
It lost me nearly 2 years of Templot development (including some testing of the tentative native Mac version I was doing), by wiping files during an upgrade (of Crossover, not Templot). That’s possibly more nuts than you are experiencing!
Sorry I haven’t been around to comment, but as you have said, the issues are with modal windows, where a dialog box goes to the background behind another window, and can’t be seen. This is not unique to Templot, and gets similar complaints from some parts of the gaming community, so it’s at best a quirk of Windows coming through on the Crossover emulation in the MacOS environment.
(As an example, if I try to save and overwrite a file, I cannot see the dialog box which warns me of this, but if I click the y key to say yes, it all works fine, this also happens when deleting a group of templates - I can’t actually see the dialog box, but it is there. I have learned to deal with this by clicking on said key, but it took a while to find out what the problem was and how to work around it.)
It’s frustrating, but then again, every time I use a Windows based machine for home use*, I am reminded how much I prefer the Mac environment (and my previous Mac lasted me 11 years, and was a lot cheaper than replacing a PC every so often). It’s all down to personal preferences: I get that MS Windows has market dominanc, partly due to the initial cheaper first cost, and that Apple is very much a smaller market. Quite what happens with future ARM-based chipsets as they diverge more and more from Intel will be interesting to see.
*PCs I use at work tend to be more rigorously controlled for updates etc, much like Apple do, and the freedom to make changes (or a hash of them!) is removed from users, so lots less goes wrong. There’s a moral in there somewhere!