I'm sure you've all see it before something like: This application is not compatible as it uses a 16bit operation, this will not work on your system, blah blah whatever.

Is there much of a way around this? I know there are rare cases of games of high popularity where people will whip up some process to create a do it yourself installer, or they'll make one themselves to save you the headache which can use your original files off a disc/disk(etc.)

I've been jonesing for the original Civilization and Sim City Classic, both Win 3.X 16bit games, and well on Win7 and now Win8.1 64bit I'm denied.

Some people have been creative in making updated installers, some work (Dune Legacy for Dune 2 PC) and others worked fine through Win7 but died on Win8 (Mark from Germany, did all those installers for Tie, Xwing and Indiana Jones games of the mid 90s.

Other than going the route of buying or pirating an old OS and throwing it inside of some VM which is just an overkill pain in the ass for a single game, can much be done?