I've been a long time PC user, and using a Mac really depends on how much you want to get out of your OS. I've used many operating systems (Windows 98, 98SE, 2000, XP, Vista, Mac OS X Tiger, Leopard), and I would rate Leopard as the best. I don't understand these "buggy" things people find with Leopard, I love it. Lots of people criticize Vista, but the 32-bit versions work with even some of my programs designed for Windows 95! If you're coming from using Windows (regardless of if you like it or not) and you already have copies of programs you like, there's no reason at all to buy versions of them for your new MBP. Get a copy of Vista (I'd recommend 32-bit Home Premium, very compatible) and a copy of VMWare Fusion 2. You can run Windows programs right in the Mac OS which is really nice and convenient. I've used a few versions of Office for the Mac and would recommend getting a copy. Home/Student Edition is $150 (3 licenses). 2008 is VERY confusing and hard to get used to at first and I was ready to throw my MacBook out the window the first few days. Once you get used to it though, you'll love it. It even has features you'd find in Publisher. All Macs come with iLife '08, which is awesome although iMovie isn't as good as it used to be for some movie-making situations. All in all, you'll LOVE your MBP. If you're coming from using lots of Windows programs (like me), get a cheap copy of 32-bit Vista Home Premium and VMWare Fusion. If not, then just get Microsoft Office 2008 Home & Student Edition (which I'd recommend either way if you do or don't get Vista and Fusion).
Hope that helps! Good luck with your MBP! Happy holidays!