So I figured I'd just share that today I found another solution that I'm happier with:
I found a 3rd party app called LightShot that manages all the screenshots on the system (available on macOS & Windows). I've programmed my own hotkey (that doesn't utilize the print screen button) so that it completely bypasses the Diablo 2 bug where it saves a screen shot regardless of the saved key binding when using print screen.
Now my OCD is fully satisfied
[RESOLVED] Screenshots with Cactus
If you are experiencing issues with Diablo II (or a Bloodline game), you can post here.
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Re: Screenshots with Cactus
Lol! Glad to hear.