@dfx I have to admit I never used any Windows prior to 3.1. My family kind of stuck with DOS until 3.1 came out. Perhaps I should mess around with 3.0 sometime just to see its differences. I wonder how many of those older era Windows games I have would run on 3.0 and not require 3.1.
Might some third party have rigged up a "y2k patch"? I feel like a simple solution might just be to overwrite the hardcoded 19 prefix to a 20. (That may interfere with stuff actually dated 19xx, but I'm not sure if that would actually break anything.)