Ah good times. I started out with one of the early ones, maybe 4.04 or something like that. Ubuntu was my first Linux, and then Mint. Unfortunately, for work purposes, I had to switch to MacOS (not a bad OS), but I still miss Linux from time to time, especially reading about that story on the frontpage about people losing access to their Apple IDs. I think I'll give it another shot soon...
I probably shouldn't say that but I have been daily driving Ubuntu for about 10 years. There are certainly 'rough' edges but anyone technical should be comfortable getting it done.
Increasingly I think Windows is an self-driving automatic car where Ubuntu is a manual car that you have to drive. Sure, you'll have to bang around under the hood occasionally but if your job is working on cars, it shouldn't be a problem.
The common refrain of Bluetooth not working is completely gone in my opinion. I haven't had to mess with BT since I put a BT dongle in and installed Blueman. My current issue is that if I boot into the most recent kernel, my Wifi doesn't work. No problem, just boot into the last kernel. I am going to guess the wifi thing is probably my fault because I _abuse_ my installation with all kinds of weird things. Again, it's a manual car that lets you bang around under the hood.
I have seen others work on Windows and it is astonishing to me how often their development environments break. I have to get on calls with them and try to step them through how to fix their environment because a) windows sucks b) it's an 'automatic car' that doesn't want you banging around under the hood, it actively tries to stop you c) it doesn't use a sh shell language so you have to specifically cater to it
Desktop users who last used, and liked, Ubuntu during the pre-Unity/pre-GNOME-3/pre-Wayland era (before 2011 or so) may not like it so much these days.
It's a very different default experience now.
While I have fond memories of the earlier releases of Ubuntu, the more modern releases have been pretty much unusable for me any time I've tried them, unless I redo the default desktop environment with something sensible. Snap certainly hasn't helped the overall usability, either. Having to make so many changes pretty much defeats the purpose of using a distro in the first place.
I've also helped several non-technical and semi-technical macOS and/or Windows users who've wanted to try Linux. The ones who wanted to try Ubuntu first ended up much happier when I eventually introduced them to KDE running on X.
4.10 was the initial release, afair :) With 6.06 (postponed by two months to "get the release right", due to the extended support cycle) as the first LTS release. I fondly receiving 5.xx-release-CDs in the mail and distributing them on our uni campus and in schools back in the day!
