Try it yourself before you buy it. It's more intuitive and less annoying for some people, less intuitive and more annoying for others. If you don't like OSX then you just wasted a lot of money compared to, say, a ThinkPad. Bootcamp sucks too due to stupid little things in the Windows drivers like only being able to use that 1.3 megapixel webcam at 640x480.
Vmware - OSx86
And while you're messing around in VMware give Win7 a go too. Anyhow, you won't be able to install from a system restore CD, you'll need a full retail copy, so ask your buddies who recently went from 10.4 -> 10.5 to borrow their DVD.
Or just hunt around for an already set up VMware image from the usual piratical bays.
The first thing that struck me is that just about anything I'd expect to be freeware is $5-20 shareware on the mac. Resolution changer for the second monitor so you don't need to fuck with the system preferences? $5. Non-Tweetdeck twitter client? $5-20. Image viewer that's not half as good as IrfanView? $10.
So rather than googling just check
Software Updates - Mac OS X - Freeware - VersionTracker when looking for a quick app that does whatever.
Oh, and install Quicksilver and Growl.
FWIW I use OSX and Linux laptops daily at work, and a Windows 7 desktop machine at home.