Definitely. I think the way microsoft brought their user base along between 1990 and 2000 from Dos to 32-bit protected mode was beautifully respectful of their users. To me it's the standard for how to change a user's preferences (maybe for social change in general). I just used Dos or win16 apps less and less over the decade and eventually my use dropped to zero. At no time did I feel coerced to leave behind what I already invested in, I just came to appreciate the alternative they were offering (the opposite of a forced OTA update). By the 2000s I could already sense a slight change in tone with how strongly they were pushing those service packs for windows xp.

Windows games worked great on Windows 2000! There were officially inofficial packages of DirectX and such - I never had any trouble with them.

I think DOS games also worked.