One feature I used to love with iPod and iTunes was you could create random playlists from music saved on PC and transfer to iPod. So if I had 250GB of music on PC, I could create totally random selection of 32GB of songs and then iTunes would copy them onto the iPod. Do you think there is any way to do this with the AK100? Right now I am copying whole albums over using Explorer and I would like to have a more "random" selection.
I do this using mediamonkey! There is a small workaround that has to be done to the playlist tho, as mediamonkey can't get the paths correct for the playlistfile.
What I do is I like you generate a random playlist of my entire collection in mediamonkey, save it as a playlist. Via right-click you are then presented with the option to synchronize playlist to AK100. This will send the songs in the selected random playlist to the AK100. You can then save the playlist as a m3u file and manually convert it to a pls file and add it to the playlist folder on the AK100 (the info on how to do this is in a comment by among others myself somewhere in this thread).
Above steps sound a bit confusing, but it really isn't all that much work!