1) Test whether the game runs on your system without problems
--it does: OK
--it doesn't:
2) Find out if it's a 2a) DOS game, 2b) a Windows game, or 2c) which system it runs on.
2a) It's a DOS game:
--try DOSBox
----it works: OK
----it doesn't: see if it's available on GOG
------GOG has it: OK
------GOG doesn't have it: see if someone's done a Windows remake and go to 2b)
2b) It's a Windows game:
--Try out various compatability modes
----it works: OK
----it doesn't: see if it's available on GOG
------GOG has it: OK
------not on GOG:
--------See if someone's progammed a hack
----------it works: ok
----------it doesn't:
------------Install a VM or a dual boot system
--------------it works: OK
--------------it doesn't: see if it's available for another system and go to 3) or see if someone's done a remake and go to 1). You may get caught in a loop here.
2c) It's a non-Windows or non-DOS game
--Install an emulator
----it works: OK
----it doesn't: see if someone's done a Windows remake
------it works: OK
------it doesn't: go to 2b)
3) Nothing works: it was a ****** game anyway