Thank you for this suggestion. It took me a bit to setup as I'm not well versed [yet] in variables. But I was able to do it and made a quick video with the results.
TLDR: The floating window in question is being recognized in the window count.
I did find though, while troubleshooting this issue, that if I use the variable %FrontWindowName% , the result returns "Display Text" whereas for all other types of floating windows and "regular" windows in Digital Performer, it returns the exact name of the corresponding window.
While using [%FrontWindowName%] it's not displaying the correct name for the window, but when using a macro I found in the forum titled "List Windows Keyboard Maestro Can se. v1.1",
https://forum.keyboardmaestro.com/t/list-windows-keyboard-maestro-can-see-v1-1/2188 that macro correctly displays the name of the window that %FrontWindowName% is not identifying.
Is that interesting or telling?
In summary, window count is accurate with regard to the windows open in the application Digital Performer, but the name of the floating window that I am having an issue with is not providing its name to %FrontWindowName%
Window Count Screen Recording