Game changer was the new EFI tools which streamlined the install process greatly. biggest PITA for me was support of USB3 in the sandy/ivy bridge chipsets, and getting a smooth initial install with various video cards, as apple has shitty, inconsistent support for AMD and nVidia. for me, currently everything runs stable on sierra which autoupdates. (i always pucker up a bit for each update though)
built a media server for video editng and digital assets, and all the hard drives, hotswap sleds, multiple boot drive configs all fits into a 4u rackmount form factor. I have mulitiple workstations where i can variously collaborate on sequencing, audio mix, photo editing, video compositing, and i would go fucking insane if i had to conform everything for the current, anemic, limited imacs for sale right now.
otoh until apple closes the hackintosh loophole with some trusted computing model in the near, dystopian future, i will be building, running, and maintaining hackintoshes. OSX install and feeding is still less of a hassle than windows, and osx still is a better workflow for us than linux.