Upload & Sell: Off
I've built several hackintoshes, one of which has been my primary photo workstation (and general computer) for years. The only real headaches are related to upgrades and updates. If your computer works one day, and you don't change anything, it will work the next day. One of the boxes I built (the latest one) was pretty vanilla hardware, as far as hackintoshes go; gigabit mb, i7, gpu that has native OS X support, legit Airport on a PCI adapter, etc. It pretty much "just worked", and upgrading from 10.6 to 10.7 was painless. My own box (q6600, older 8800gt) is still on 106.8 probably wouldn't upgrade very well, and I haven't had a chance to put Lion on it. Point releases on the OS are rarely a problem, except for some audio or networking issues that are easy to resolve. So if you're looking for a laptop, look around of tonymac, insanelymac, etc, and find one that people have had good luck with. If you can find something that fits your needs, you should be fine until 10.8. That being said, Apple and PC laptops are relatively comparable in price these days; not a lot of "apple tax" any more. So while the things you cheaper laptop offer will probably "just work", it may simply be missing some things (FW800, multitouch track pad, etc).