I'll put my 2 cents. I did a hackintosh for fun a long time ago... it sucked. This time round though, I needed a good NAS but more than just a NAS so I went with a hackintosh. Honestly, it was really easy for me. I've build PC's before and having been in the hackintosh scene previously, it wasn't that bad at all. About as "easy" as I had expected. I put it together and installed the OS in about 1 evening. A few hickups here and there but got it running just fine. Total time spent, about 6 hours of my active time (build and install).
Now the what you're using it for, that's the big one. If it's for daily money making use, I'd never use it. What I needed was something to store files, be a plex server, possibly transcode video, and also have the ability to run background automated stuff (apple script). I thought about replacing my dying mini (2009, but it's really on the HDD's that are dying) but I really wanted the ability for multiple desktop drives, but I also wanted the ability to process some things (x-out for a nas).
I've got stuff working just fine so this setup is going to get the OS drive cloned, and I'm going to lock it down so no updates except for application updates (ie plex, handbrake, etc.). Maybe.. just maybe... I might toy with Yosemite during my Christmas break, but it'll need to be well supported before I'd entertain an update.