Will the computer be in the same room as the rest of the system?
If not, AE+Toslink to a DAC of your choice makes sense - provided you're happy with your remote interface. Apple remote can run on a laptop or i-phone and works well. The Sonos system is another good choice for distributing music with control (it has a great user interface), although $ can add up quickly and you'll probably still want an external DAC for critical listening.
If the server will be in the same room as the rest of the system, you might want to consider a USB DAC hard wired to your computer.
To your DAC question: I own a Benchmark and it's very, very good, but is on the lean but revealing side. In my system, it's a great match, but YMMV. I also use a DacMagic in a different application which is less expensive and might be a good choice for direct connection via USB, as it has such an input. It is on the rounder, warmer side of the spectrum and is IMHO a great value.
Good Luck
Marty