Rbstehno, you almost had me until you recommended toslink to hook a computer up to a DAC.
I have been into computer for quite some time, and toslink sucks for transporting data from a computer to a DAC. I have tried it, and the current way I am doing it (with Empirical Audio's Offramp Turbo2 via USB port) is so superior, it is not even funny.
Microsoft has little to do with my ripping and playback per se. Foobar2000, my playback program, was developed by a 3rd party and is very stable (in it's current version). Exact Audio Copy was also developed by a 3rd party, and is ultimately stable as well. These programs have been developed over 8+ years by people who are extremely dedicated to both. I have never gotten a blue screen running either EAC or foobar2000.
"there are many other ripping programs that run on a mac so that is a non issue, and if you wait, there will be a new 1 tomorrow" - 1,000,000 bad rippers do not equal 1 excellent ripper. Please name a ripper on the Mac that has over 8 years of development behind it. Ripping programs for the PC are a dime a dozen as well, but I freely admit, most of them are not that good or just average. I have tried quite a few for comparison.
Also, do you realize how much of a difference a great aftermarket power supply makes for a music server for playback? Unless you have disassembled your Mac and changed out the power supply (I imagine it voids the warranty like most other Apple products if you take them apart), you have no idea.
Interestingly, I do like Macs. And if someone demonstrated to me on a Mac a playback program as good as foobar20000 and a ripper as good as EAC, I'd consider switching to a Mac. I would still want to change out the power supply.
Heck, if I could get better playback and ripping using LINUX, I'd do it in a heartbeat. Last I checked, there are quite a few rippers and players for LINUX. Still, none as good as the ones I mention above.