I think it's interesting to compare Windows ME to Mac OS 9.
Although they are quite different, they both historically fall at about the point in each respective company's history. They were released about the same time. Windows ME represented the final incarnation of DOS-based Windows, while OS 9 was the end of the line for the "Classic" Mac OS. All future Windows development was NT based, while all future Mac OS development was in OS X.
That's where the similarities end, though. ME is often the butt of jokes, while many folks still hold OS 9 in high regard.
As for myself-at the time my Dad was a Microsoft "Action Pack" subscriber(I think that's what it's called) and basically got a binder every few months with CDs for about every current MS product. He had no interested in Win2K, so I installed the Beta version they sent him and used it for a while then upgraded to the full release when that came in.
Around the same time, he upgraded his computer to Windows ME, and had no end of trouble with it. At the time, his tax software(he ran a tax preparation business from home for a long time) wouldn't run on 2000 but would run on ME, so that's what he used. I think at one point he even downgraded to 98SE because ME gave him so many fits.
I briefly dual-booted ME and 2000, but liked 2000 a lot better and stuck with it. 2000 really never gave me any issues at the time.
We both upgraded to XP when it came out and never looked back.
BTW, even though I had no issues Win2K at the time, I still use it regularly as we have an instrument computer in the lab that is still running it. I needed to get some data off of it the other day, and had a terrible time getting a flash drive that was readable in it. It seemed to object to the fact that the drive I was using had ever even been in a Mac despite the fact that it was formatted FAT32/MBR. I ended up having to format it in a Windows 7 computer, but was only able to get 200mb of the 8gb on the drive. Desperate times call for desperate measures, and when I'm dealing with 20kb .CSV files(spreadsheet ASCII) 200mb is plenty of space.