Cool, it is contagious...
I was talking about your post
Allow me to explain, you asked "Were there any changes with Activex settings made at all during the installations?"
Which I concede might be a interesting course of questioning, if the installations in question didn't predate any sort of ActiveX by nearly 20 years! Additionally, no part of ActiveX- or COM, for that matter- is used by the DOS emulation subsystem, so changes to those settings wouldn't affect them (and I question what exactly constitutes an "ActiveX setting" since to my understanding none exist, except within other programs. (Internet Explorer, for example).
My best guess might be because of the way windows deals with older software installations. it can "detect" some game installs- notably, Duke Nukum 1, 2, and 3, and sets certain compatibility settings to config.nt and autoexec.nt that will change how all DOS-based software works. autoexec.nt and config.nt are profile-level, I believe, which would explain why the issues are reproducible in a new account.
It could very well be that those changes are needed for the other game, which isn't something Windows takes notice of being installed. Best way to confirm this would be to use Process Monitor (Filemon is deprecated) and capture events for the initial installation and then search those results for a file access to any config.nt or autoexec.nt files.