Based on your statements it does not appear you are ready to make the switch. This is more than a "lifestyle" change or a fashion statement. The new Intel Macs are awesome in everyway. I would disagree that OSX would be alien and difficult. Macs are designed to be user friendly (Simple and functional). Plus the Apple website has tutorials. Also most software companies usually allow you to switch platforms for free, like Adobe and Capture NX. I think I paid $6 shipping to switch my Photoshop CS3 to a MAC version.
I've been a PC user since 1995 and like you have always looked at the price tag. I also looked at the specs and software etc...Back then it was a no brainer, but Intel Macs bridge the gap in power and in software.
Last year I bought a brand new Dell Desktop, very high end running XP. But like most PC's, I was always fixing the dam thing. I realized that I'm always fixing my PC's, very frustrating and not very productive. I'd spend hours fix little problems here and there, which affected my productivity. You can buy a great PC, but you have to run Microsoft, that's the downfall.
Anyways, I went out and bought a MacBook Pro, no more fixing. I don't even touch the Dell desktop, except to play itunes when I'm working out. That's a waste of $1200.....I could sell you my Dell.
Also think about the future. Cheap monitors are just that, "cheap." If you want to get "What I see (on monitor) is what I get (print)." Skip the Dell monitors. I bought a 20"Ultra sharp ($399) based on reviews, but later found out Dell uses various panels in the same model. I got a Samsung PVA. Good viewing angles but not capable of 16.7 million colors. (.7 is key). Anything less, the moitor is mixing (forgot the technical term) to create colors. I ended up buying an Apple Cinema (which is a minimum standard).
I run CS3 Photoshop, Indesign, Lightroom, and Capture NX2 with no problems.
Also Bestbuy is expensive! BHPhoto or Dell
When buying a MAC, the saying Time is money is so true!