Before switching to Ubuntu late last year, the last time I'd used Debian on the desktop was around 2000, so it's true that my experiences with Debian are mostly 90s-era. However, it's still the case with Ubuntu that it's common to install something, try it, and then be unable to get things back to the way they were before (mostly speaking of desktops, WMs, and themes, here). It's not uncommon to allow Update Manager to update things and then find that programs that were working fine suddenly don't work. This happened to me just in the last month with Wine, and happened a while before that with PulseAudio.
I have the patience and time to spend a day changing my config until things work again, but it's certainly a ways behind both Mac and Windows in this area. Additionally (while I'm venting), Ubuntu trains you out of reporting bugs because if you actually reported a bug whenever things went wrong, it would be a part-time job. I actually had fewer update problems with Gentoo ca 2003, though at the time I had things to get done and just wanted stuff to work, whereas now that that I don't depend on my home system to make money, I find fixing the problems fun. :)
I have the patience and time to spend a day changing my config until things work again, but it's certainly a ways behind both Mac and Windows in this area. Additionally (while I'm venting), Ubuntu trains you out of reporting bugs because if you actually reported a bug whenever things went wrong, it would be a part-time job. I actually had fewer update problems with Gentoo ca 2003, though at the time I had things to get done and just wanted stuff to work, whereas now that that I don't depend on my home system to make money, I find fixing the problems fun. :)