I've been tinkering about with Linux distributions for some years now. I'd always get the system "just about working" and lacking the knowledge and inclination to tweak it until it was right, I'd eventually give up. Of course I'd be running one of the X-Windows GUIs but MS Windows was always more convenient for me, I'd become lazy relying on GUIs to do all my configuring. Or was that just my excuse for not being technically competent enough? More than likely a bit of both. There were times where I'd sat down and started reading various HOWTOs, trying to get some service or other doing just what I wanted it to, but then there'd be dependency errors or even worse, no errors at all (at least visible ones) - the thing just refused to work. Nothing I'd read up to that point had referred me to the existence of error logs, let alone their locations.
More recently I'd installed Debian on a redundant piece of kit and had it running on the network doing bits and pieces such as serving web pages. No need for a keyboard, mouse or monitor, I could ssh in from any of my Windows machines to tinker whenever I felt the urge. The only thing I couldn't get running was IMAP server, but that wasn't too bad as my mail is collected on an external server.
Then one day disaster struck. My main desktop PC gave up the ghost. Actually, not completely, but became very unstable, shutting down all the time. I appear to have an overheating problem in the CPU but that's by-the-by. So I connected the whole human interface gear up to the Debian box and started to use that as the main desktop PC. I never mentioned earlier that I quite like Debian, installing things is relatively simple with the 'apt-get install' command. Anything that couldn't be installed that way usually had an idiot's guide to unpack and install. I even managed to compile a couple of packages from source code. Get me, eh?
So I loaded up the X GUI on the Debian machine and was running with that for some time. I had a few office packages on there, Open Office, for example. The only thing I was missing were games like Medal of Honor, things I played online a bit. But online gaming is difficult when you're out at work for 10/11 hours per day and need to be up early, not to mention spending "quality time" with the wife. So it wasn't so bad. Until I wanted to use peripherals. It took me ages to get my printer working. The scanner and any USB drives I had no success with at all. I'd trawled through endless forums and anything else that Google through up at me. Nothing.
Then one day someone suggested 
. Anyway, after finding out how to explicitly set a global proxy in the Ubuntu configuration things started to run a bit smoother. The printer was set up straight away, the USB drives are plug & play (just plug them in and up pops a file browser window) and after installing a package the scanner works fine. The only thing that's puzzling me right now is sharing the printer across the network. Oh, and the IMAP server again. I think both issues have more to do with me needing a little more education on configuring these things.
The whole installation process is easy, just as easy as Windows I'd say. Adding new packages, too, can be done using a package manager in the GUI, or 'apt-get install' using a terminal window. Updates and upgrades can be done just with a few clicks of the mouse (and entering the administrator's password). I'd really say that Microsoft have a genuine contender for Windows, Ubuntu is very user friendly and simple to set up. The support seems very good too, although some users new to computers might not feel comfortable about using IRC for live support.