Having never used Windows Home Server, but the full version of 2008; what makes WHS so great for serving media files, over just a standard Windows 7? Microsoft doesn't make DLNA software which understands MKV or FLAC files do they? So you're still reliant on 3rd party software to do the serving. Windows 7 has H.264 and Dolby Digital Plus codecs installed by default, so just Haali Media Splitter is all that's needed for most MKV playback.

Pioneer PDP-5020FD, Marantz SR6011
Axiom M5HP, VP160HP, QS8
Sony PS4, surround backs
-Chris