I assumed that building and maintaining a hackintosh machine would be a pretty major pain in the ass but my friend says it was no more difficult than building a bespoke Windows machine as long as you did a tiny bit of up-front research on parts.

It's no different from building any other PC, except for the restrictions on parts, like you said.

Nowadays you don't even have to worry much about that - there are high quality, in-depth guides that will walk you through the entire process step-by-step, if you need them: http://lifehacker.com/5841604/the-always-up+to+date-guide-to...

I've been maintaining my Intel i7 based Hackintosh (currently running Lion) since May of 2009, and the only time I've really had any asspain was doing major OS upgrades. I went from Leopard to Snow Leopard, and then to Lion, and each time I basically spent the better part of a weekend on the upgrade.

While this box has held up fine for my OSX work, it's getting long in the tooth for Windows gaming. Now that Mountain Lion supports high end graphics cards like the nVidia GTX680 out of the box, I'm looking to build out a new Ivy Bridge based Hackintosh that I'll also boot into Windows for some high-end gaming.