mbee:if the central server doesn't know your songs, they will never appear on a selection (same problem here with iTunes' Genius)
Thank you ... I did not know that nor noticed it ... yet ... but now I know I am sure I will notice it 
Another alternative is "Genius Mixes" where you get 16 pre-selected combinations of your tracks - these are where iTunes has classified recordings as "Pop", or "Classical" or "Jazz". When Genius Mixes was launched with iTunes 9 (I think) I posted a description of how my collection had been analysed and grouped, and my surprise with the results.
Normal "Genius" usage where you select a specific song (and if it is known by iTunes, that bit I knew, I just had not connected the dots). iTunes then makes a dynamic playlist of songs compatible with your selection, and you can play it immediately, and you can also save that list as a static list and play it again.
So my wife likes the Genius playlist I created for her from a "Madame Butterfly" seed track.
On the other hand, I have created a number of smart playlists using filters on the iTunes meta-data, and then I introduce variety by sorting the list by ascending play count so that there is an ever changing list of least frequently played tracks in categories like "opera", "jazz", "classical", "soundtracks", "60s music", etc
First B&O (1976) was a Beogram 1500 ... latest (2011) change has been to couple the BL11 with the BL6Ks *sounds superb*