I was two years out of college. I used to use DesQview; outstanding program for multitasking DOS apps. I remember some tech writer at PC Mag (or maybe PC Week) saying that for stability, it was better to run multiple instances of Windows in DesQview with one application each, than to try and run multiple Windows apps.
I could not understand how, for business use, Windows up to 3.0 was remotely acceptable, as often as it crashed. WFW3.11 was a little better, but not until 98 did I begin to "like" it. Apparently, I'm also one of the few that never had a problem with WinME. I skipped Shista due to known compatibility issues with software / games I use (e.g. Sacred), but Win7 runs them all no problem.