For example, if this is your primary work station for completing somewhat time sensitive things (books, courses, weekly podcasts, etc.) would you feel comfy?
What type of worst case scenarios are we looking at if an update fails?
I'm not saying you shouldn't do it, just that there is no guaranteed safe path and you'll always be at risk for an update borking your system. The best you can do is make maximally informed decisions and prepare for the worst. And ideally have your hackintosh be a secondary machine that can die at any moment without screwing up your life.
It's a great hobby project but (like others have said here) it's something you do because it's a fun and interesting ongoing challenge. There's really no context for anyone in which building a hackintosh is a rational choice made for purely pragmatic reasons. FWIW, I wouldn't consider saving money a pragmatic reason- the ongoing time and risk involved will always exceed whatever money has been saved, unless your time has little value and you have nothing to lose (which admittedly is the case for some hobbyists or students, but good luck getting anyone to admit that :).
I put together the above for around $750 over 2 years ago. A somewhat equiv. MBP is like $2,750 (and would still be worse in nearly every aspect spec for spec).
I value my time and sanity but some of these stories make it seem like if you have a good combo of hardware it's an hour or 2 per year just to handle some updates and a bit of chaos. I think I'm willing to trade that to save nearly $3,000 since for me it would be buying a MBP vs hackintoshing my current machine.
The problem and cause of hesitation is due to it being my only machine capable of doing my primary work.