I avoided Windows like crazy until Windows 2000 came out because prior to that release the idea of using an OS where one process could crash the system at any time seemed ridiculous (post my Amiga days), and running NT was only for "enterprises" (at that time).
Ah, the MS OS/2 2.0 fiasco, though my favorite limitation of Win9x is actually how it depended on DOS which allowed Caldera to continue the lawsuit against MS.
Ah, the MS OS/2 2.0 fiasco, though my favorite limitation of Win9x is actually how it depended on DOS which allowed Caldera to continue the lawsuit against MS.