Actually if you follow debian/ubuntu at all, their nearly as userfriendly and easy to use as windows is for any average user that has NEVER been on a computer before today.
Now that's not the same as what most of us here would be classified as, yes I would myself format and reinstall any OS so I had it setup how I prefer it to be..
But in all honesty I could install a debian or ubuntu desktop without any extra tweaks just basic installation on my mother's computer put launchers for Firefox, ThunderBird, and OpenOffice on her desktop and she'd be happy and fine not really realizing she's on OMFG LINUX@! I dunno what to do now!.
They find hardware extremely well now and autoupdate and do so pretty well without much user interaction now the same as windows for normal usage etc.
As far as navigating to software and things, debian and especially ubuntu is extremly user friendly now out of box..
Keep in mind im saying "user" not power user or uber geek here.
Just trying to show that there isn't much reason anymore that windows has to be the only option for "average joe user" who at some point will run into some problem and be stuck because it's linux, that's just not the case anymore.
Hell even PC-BSD is getting closer and closer to being userfriendly in this manner also..
As well as a few other *bsd's, but their still a little bit behind on the user friendly front but not to far.
As far as microsoft goes I will never give them another dime for an OS or anything if I can help it.
The only thing I would consider is something new on the media front in regards to movies/music as long as I can get around drm, other wise they'll never see another penny from me.
