Free OS to play with...

Why would you bother going through all the trouble and torment - as well as spending the money on the disk to use an OS that's no better than the free alternatives?

exactly - getting OSX to run well on a PC is an exercise in frustration.
 
Try FreeBSD , in my experience it's one of the most complete operating systems I've used. There is load of documentation to help you out, strong community and generally good hardware support, albeit not as a good as Linux. It also have the choice of compiling software or using binaries which provides an added bonus.

Linux wise, I use Gentoo. Whilst I appreciate how much Ubuntu has done for Linux and how well Canonical has put together all the GNU software, Ubuntu just doesn't float my boat. If you persevere with Gentoo, you will learn a hell of lot, mainly because you have too but it'll certainly keep your attention.
 
I don't know about you lot but I find the KDE Desktop to be a much better alternative to Gnome as I prefer it's feture set. If you've not already tried KDE you might want to try Kubuntu as this is Ubuntu with the KDE Desktop.

If you already have an Ubuntu distro on your system that uses the regular repo's then you can run "sudo aptitude install kubuntu-desktop" to install KDE onto your system.
 
I don't know about you lot but I find the KDE Desktop to be a much better alternative to Gnome as I prefer it's feture set. If you've not already tried KDE you might want to try Kubuntu as this is Ubuntu with the KDE Desktop.

If you already have an Ubuntu distro on your system that uses the regular repo's then you can run "sudo aptitude install kubuntu-desktop" to install KDE onto your system.

+1 Kubuntu is a nice transition from Windows
 
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