When I do encounter a problem, the answer is almost always available after 5 minutes on Google.
Following the herd leads to an easy life. Go figure.
Personally, the difference I see since I switched to Debian (six years ago) was that I had less problems than on Windows, and more importantly, that I could actually fix those problems instead of having to get used to them.
My Windows 7 desktop, which I barely use compared to my Debian laptop & VPS, still wastes much more of my time with maintenance and random bugs.
I once had to start Windows in Rescue Mode and do some weird stuff there just to get Steam back running. It failed to start suddenly and seemingly without cause. For a while (some years ago) I couldn't boot Windows at all until I unplugged a dvd-drive (linux was running fine) - I still use that dvd-drive, windows starts with it again. I bought GTA 4 and couldn't play it because Games for Windows Live wasn't working (still doesn't, but i found the hidden offline-mode). Sometimes I can't delete files in Windows with no cause whatsoever.
At the same time, I'm using a rock-stable Ubuntu LTS with a custom "desktop environment" on the same hardware and never had any real issues i still remember. Oh, thinking a bit longer about it, there were some issues when upgrading to this lts: plymouth didn't stop itself (i had to end it via the rc.local) and pulseaudio didnt work (switched to alsa). That's about it.
Following the herd doesn't lead to an easy life, the herd willingly runs down a cliff.
Guess it is not so bad anymore, but if you liked Ubuntu in production servers, going the route of a small window manager could be more your style (don't know if I'm stating stuff obvious to you, just in case).
The most stable computers I've ever owned have been those that I've built myself, while 90% of my repair work comes from Dell and HP computers that barely last 2 years.
I don't think I'll ever buy another Mac desktop, because I'm so thrilled with the ability to "look under the hood."