Probably you used Linux at the time it wasn't very mature. I'm running Gentoo now and never had to reinstall to fix things. With modern computers compiling is very fast, most software compiles in less than a minute. I spend more time solving binary compatibility problems with CentOS (at work) than compiling stuff via portage.
I recently bought a new video card (nvidia), plugged it and then booted linux. It just worked out of the box. Then I proceeded to boot windows, it started on a low resolution video mode because the current driver failed. So had to download and install latest drivers manually. The whole procedure took like 3 or 4 restarts.
That's the huge advantage of distros without discrete upgrade paths. I have the same Gentoo install on my desktop since I built it in 2008. Meanwhile I tried Ubuntu on my laptop for a couple of years and every time a new version came out, I tried to upgrade only to find my system borked, hours wasted, and ultimately my giving up and doing a fresh reinstall.
And yes, so many more things work "out of the box" today than ever before (as long as it isn't ATI/AMD :P). The Linux ecosystem has grown and improved incredibly over the last few years. I wouldn't dare argue whether it's better than OSX or Windows, but I can comfortably say that it has advanced a much further distance in the last few years.
I recently bought a new video card (nvidia), plugged it and then booted linux. It just worked out of the box. Then I proceeded to boot windows, it started on a low resolution video mode because the current driver failed. So had to download and install latest drivers manually. The whole procedure took like 3 or 4 restarts.