@mitu geez that was quite a fast reply/clarification, no sooner had I walked away from my comp/posting then I realized I'd been remiss in not asking another even more pertinent question:

Have you all had any/many MicroSDs you were using on your Pis FAIL? (I'm guessing there are some informatively depressing threads here that can share some stories about as much...?).

At the end of the day, perhaps whatever larger MSD I get for these CDROM games (granted, I guess we'll see how many of them have stood the test of time to be worth keeping), ideally I may even have enough space on it to also fit what's on my current 128gb, who knows (and in turn, likely another 512gb/whatever to back THAT one up).

Ultimately, memory is never quite as pricy as the time spent collecting it...

There is also the Free Heroes 2 engine (Fheroes2) that you can compile on Raspbian and make it work. I have succesfully tested it both in Raspbian desktop(X11) and in Emulationstation. It runs best in Raspbian desktop(X11) since running it in Emulationstation is too slow in speed.

I might as well create an install script like i did with Hexen 2 Hammer of Thyrion source port.

By using the Free Heroes 2 engine you will not be needing dosbox as this will run Heroes 2 natively through the source port.

Let me know if i can be of any help to you.