No, I'd never buy a 'real' Mac desktop, vs. a Hackintosh, unless Apple made one that actually suited my needs.
When I see some discussions like this, I honestly think people must be talking about something else, because with the Hackintoshes I've built, I must have done something right, compared to what some claim as their experiences.
It's nothing like what I've experienced. Maybe it's just that I can read, follow instructions, and pick hardware that works, rather than pick components at random so I can complain about it not working, and gripe about how much time I had to spend reinventing the wheel? I really don't know, but I'm guessing it's something like that.
My signature Hack has worked perfectly since day 1. I spend approximately NO time messing with any kext files, or with the terminal or worrying about having to 'hack' anything. I've built hacks for other people and had not a single complaint with any of those systems wither, all of which keep right on performing for their owners.
My main hack has enabled me to get work done faster than any Mac I've used at work.
Every time some OS update comes out, I'm not really pulling my hair out because *gasp*! A number will change! It's funny, dirty little secret- my work got done just as fast and just as well using 10.5.1, 10.5.2, 10.5.3... and now 10.5.4. Will 10.5.5 suddenly do my work in half the time, give me a shoeshine, and shoot rainbows out of my DVD drive? No? Then it's likely I won't curl up in a ball and cry if I can't upgrade my Hackintosh to it the second it comes out. Sooner or later, I'll be running that update too, and I'm guessing in reality, it'll be much like the previous ones: "Oh gee, look at that About This Mac box. A number changed. Whoo hoo that's cool. I suppose something, somewhere is... err... different? better? faster? cooler? Okay, enough admiring a number.. now back to work..."
It took a modest amount of reading and asking a few questions to set things up correctly to begin with- much smarter people than me have already figured out most anything that's all that difficult. But once it's set up, it's set up. Really, what is all this constant hacking people claim to be doing? Is that really for real, or are most people just digging themselves out of a mostly self-created hole? (IE: didn't follow a guide correctly, didn't choose compatible hardware, had to update to see a number change but little else and then borked a working system, etc. etc.)
I purposefully chose hardware that other people reported as working, so... I dunno... it works. Go figure.
My experience is that Apple simply doesn't make a system as powerful as what I can build myself, for the price I can build it. That's not to say the MacPro isn't an amazing machine, but it's really not $3,000 worth of amazing compared to a midrange $600-$1,000 Hackintosh that's a little more realistic for my needs. I'm not knocking the MacPro- just I don't need the high-end, when a mid-range works better for me and costs much less. All of Apple's other 'desktops' don't work for me in the least.
IF Apple came out with a mid-range, headless, expandable, upgradeable machine that was as good a deal as say a $1,000 range Hackintosh, I might consider buying it. But they won't- that's not their business model, and I don't really blame them. But it also means I won't be an Apple customer for a desktop.
Now, a Macbook is another story. If I needed a new laptop, I might consider a Macbook. DIY laptops make very little sense, so it's a matter of buying something pre-made no matter what, and Apple does make very, very nice laptops.