I've been lucky in that my Hackintosh's working 'uptime' has been pretty great over the past 3 years. That said, I've had a couple of OS updates putting my desktop out of commission for a day or two - I would never consider it for a work machine.
With today's MacBook upgrades, I've ordered a 'real' Mac and reverted my desktop tower back to Windows gaming box duties - the 'fun' of hackintoshing quickly fades once you've done it for a few years and just want to know your computer is always going to boot when you press the power button, especially if like me you use OS X 99% of the time.
Maybe I'm just stupid, but as far as I'm concerned folks with hackintoshes who haven't had a boot breaking issue occur are either lucky, or it has yet to happen to them. I deliberately built the most 'golden' of mainstream hackintosh builds (close to identical to the Dan Benjamin one folks are linking here), no custom kexts, used Clover, still had the occasional issue.
Given Apple are moving to ever more intertwine custom hardware into Macs (touchbar, touch id, secure enclave etc), I think the future of hackintoshing is probably going to be harder than it is today.