I personally used to hate Apple and Apple products; blindly I despised them because of all the stereotypes against them. Many of the stereotypes are true, and for the most part, all the things I used to dislike about Apple - overpriced, underpowered, etc - are still true as well. But once I got into the whole hackintosh thing and actually tried using OS X for an extended period of time, I realized it was much better than Windows in many ways. I am not one of those people who gets viruses and has a slow computer and blames MS for it. I know how to make my computer run as fast as it possibly can at all times. I know how to optimize windows, I know how to work with the registry, I know how to customize everything to my liking, on and on and on. But like the OP said, OS X seems to require MUCH less upkeep. And as cliche as it sounds, many things just WORK. Quick example - I needed to use my phone as a bluetooth internet modem while on vacation and without wifi. At the time I had my ASUS 1005HA with windows 7/hackintoshed 10.6.2. I was able to make it work in both, but with OS X it literally took me two seconds, whereas in Windows I had to do all sorts of garbage like look up what number the computer should dial specific to my carrier. OS X seemed to know that info already without any input from me.
As for the MBP? After using OS X and falling in love with it, I realized there was literally nothing I needed Windows for that OS X couldn't do EXCEPT gaming. I love my gaming PC, and need to dual boot so I can game. But now that Steam is coming to the mac and all my most popular games are getting ported, I realize the switch would be easier than ever. If I need anything else windows related, I have vmware. I used to pride myself in knowing the ins and outs of a "complicated" OS like windows, knowing how to do under-the-hood stuff that most people call geek squad to do. But in reality, its much easier to have all that stuff done for you. Sure it's fun to tinker around with an OS, but at some point you outgrow it and want something that doesn't require constant maintenance and fine tuning. The MBP will fit my needs perfectly. As a notebook, I really think it's the most well-designed laptop I've ever experienced. The biggest selling point for me was easily the trackpad. The trackpad has been the biggest downfall of any mobile computer for me, and Apple solved that problem in my eyes. I actually look forward to not needing a mouse anymore. I love the gestures and the feel of it.
There's more stuff I could say, but I'll end with this: despite all this newfound appreciation for Apple's products and its OS, I still hate many things about the company itself. It's the price you pay, I suppose, to get a higher end machine with such a good OS. Either way I can't wait for the MBP to get refreshed and begin a new stage of personal computing for myself.
I would like to second everything you said as all of that pertains to me as well. My first encounter with a mac was a friends ibook, which he used to swear by daily, and somewhat annoyingly, as fanboys do. I dismissed him for years, simply unconvinced that a mac had anything more to offer, even though secretly, my hatred for Windows (XP) was growing and growing. I never really considered him computer savvy, so I immediately assumed that mac os was designed for the "computer illiterate", and simply Windows, despite all its headaches, was something to just tollerate. Hell, its what most of the planet was and still is tollerating.
Luckily I lost that mindset as soon as I went to a school with mostly Apple computers at our disposal. I quickly learned that there is nothing you can't do on a mac, except do it better or faster than on Windows. And now I look back at all that time I waisted troubleshooting this or that, I will never go back...