I just recently picked up a WD TV Live. It's an impressive little box, but the audio playback over a network is definitely not up to snuff.
I share my music from my PC and never have any issues listening to all of my music in Shuffle mode with XBMC (on the original Xbox!). I have 912 albums (14943 tracks), all meticulously tagged MP3 files, organized in individual folders with a high quality folder.jpg. I don't use embedded album art because I think it's a waste of space.
Although WD TV Live displays the album cover while browsing, if I play an album, it doesn't display the album art. No big deal, except that this is the only playback mode that works for me. If I hit Play on my entire My Music folder, it works for a minute or two and then throws a "This folder cannot be accessed" error. My next thought was to create an Everything playlist and try playback that way. If I keep the playback mode set to Normal, I can hit Play on the Everything playlist and it quickly queues up all of my music tracks. If I try to set playback to Shuffle prior to launching the playlist, or after playback starts, it basically freezes after playing the one track.
Once I understood that there is no Media Library through a network share (unlike XBMC), my next thought was to try installing Tversity, which I've used before with good luck on my Xbox 360 and XBMC. One bonus with Tversity is that it displays album art for every track, with only a folder.jpg to work with. When I try to listen to all of my music tracks in Shuffle mode, it almost seems to work! It sorts all of the tracks alphabetically, so the first track played is always the same, but the second track is random. Unfortunately, after that first track Tversity goes into a "one track repeat" mode and will only play the second track over and over again, whether I hit track forward or back.
Maybe I'm doing something wrong? Is there a different way I should be going about playing all of my music randomly? The WD TV Live is a brand new product, so I'm not expecting miracles, but I'm hoping that someone over at Tversity will eventually get a hold of one to test out.
Thanks for your time!