I've only used DOS (in and of itself) for recovery purposes, although I now mostly use live Linux distros, as DOS doesn't support NTFS.
However, I practically grew up on Windows 98 (first edition). Those were the days... you could tell by listening to your harddrive how busy the system was, you learned to appreciate those magical and mysterious sounds coming from the dial-up modem, and you didn't even have to go through any activation crap to use it.
Mine even had an added tape drive for extra storage (until it broke :(), as well as a CD-R/W writer, which could be used to transfer files to other computers or make backups of music CDs. Heck, I can count on one hand the number of times I had to deal with DRM problems.
Sadly I had to retire that old machine, as it seems to be suffering hardware problems. When you plug in the power cord, it starts shutting down and rebooting rapidly, often 1-10 times per second. I suppose it was old and slow, anyway. RIP.
I won't be forgetting those days anytime soon.