Reply 20 of 53, by radiounix
Looks like everyone has given reasonable advice. Period correct for that machine would be a copy of DOS 5.0, and with 4MB of RAM it should run Windows 3.1 adequately as long as the software is simple like Word 2.0 or Windows Entertainment pack. Later things need protected mode and/or fast 386 level performance.
It should run most games through 1992, including games with VGA graphics and fluid action. Certain advanced for the time games like Wing Commander, Wolfenstein and Stunts will execute, but probably will prove unacceptable by modern sensibilities.