tl;dr: After a lengthy time away from the tonymacx86 community and hackintoshing in general, attempting to install macOS 10.12.4 from scratch was the easiest experience I've ever had with a hackintosh.
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Reviving this thread to post an update:
I left the community for a few years (previous post here was in June 2013) because I was constantly frustrated with things breaking or not working and having to re-install OS X every few weeks because of a problem I couldn't solve. This took a toll on my weekends and my personal life as well. Ultimately I stepped away from my hackintosh, and nuked my OS X partition so I didn't have to think about it again. Time passed and I ended up getting a new MacBook Pro and a new job.
Throughout my time away from my hackintosh project, I always wondered if things would eventually get better in the community. I constantly wondered if it would be easier to maintain over time, or if hardware would start to become more compatible with OS X/macOS. With the release of macOS Sierra (10.12) I decided to take another look at the hackintosh community and see if I could revive my project once last time, otherwise I would just continue on with life as usual.
Fast forward to this past week and I have a fully functional 10.12.4 Hackintosh using my existing hardware (sans my PCIe wireless card which is no longer compatible as per
this thread) and even have iMessage working. This was completely due in part to how succinct and easy it was to follow the
installation guide, and having hardware that was 95% compatible already.
I'm going to update my main post in this thread with my process soon to reflect the ease that was the setup here
Time has indeed made hackintoshing easier. Clover is now the bootloader of choice and works very well.