Offended by a Mac, Josh? My whole life runs on OSX and iOS. Your plan for new hardware sounds solid: I actually am contemplating turning an old MacBook into a music/video server. I'd just suggest that before you purchase the new OSX, check the processor and makes sure it meets the requirements... I think the most recent OSX incarnations require the Intel chips that Apple switched to using a couple of years ago...
Kablume and everyone else dealing with medical issues: I hope you guys get clear answers and start feeling better soon.