I can see different ways to solve your complex shuffling use case. It's quite similar to nix's requirements in the post above.
Because we're trying to avoid adding too much complexity to the server, different new projects were discussed to make PShuffle more customizable. The first one was a Lisp interpretor that would allow all collection operators to be written in Lisp, and clients could write and save their own on the server. Obviously, it's far from being trivial, and we didn't get enough GSoC2007 slots to have it sponsored this year. An alternative could be to move the PShuffle inside a service client, which is a new GSoC2007 project by Ning Shi, which I'm mentoring. Clients could then rely on a more customizable client to do the shuffling, or even write their own shuffling service with special rules like the ones you and nix proposed.
As long as you either tag (using media properties) the media or put them in a dedicated collection, i.e. as long as they can be identified using collections, there isn't any reason why crazy shuffling methods wouldn't be possible :-)
The collections thing with binary operators sounds also really useful. It would even be better if there were relational operators which could work on ID3 tags. Then could tag all my tracks as "Live" or "Studio", and with a relational '<' ID3.YEAR operator, easily have a collection of "Pre-1990 Live U2" for instance.
The filtering operator work on media properties, which are automatically extracted from tags (ID3, Ogg comments, etc). So your use case is already supported by the current state of Collections!
Of course, with all these features there has to be a really, really convenient user interface, otherwise it's just too much trouble to bother with.
Of course, it's an important point. Work is still needed in that area, but it's certainly possible. So far, the text pattern syntax is one powerful way to build collections.
(artist:"Pink Floyd" l:Meddle) OR (genre:Rock AND +compilation) OR (title:The* in:Playlists/Foo (NOT year>2000))
Builds a collection containing Meddle by Pink Floyd, all media that have "Rock" as genre and which are flagged (using a media property) as compilations, and all media in the Foo playlist whose title starts by "The" and which were release prior to 2000. Note: the AND is implicit when several conditions are put in a sequence.
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