Using WME9 to stream audio files in random order

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I'm sure this is a simple question, but for the life of me I can't
seem to find an easy answer.

I want to stream MP3's from one machine to another, in random order -
I can make WME9 use a custom session that streams an MP3, but to make
it do multiple files I have to enter multiple sources, which I don't
want to have to do by hand.
I'm assuming that I can't make a session pick files at random, so is
there some simple way I can specify the file on the WME command line?
Or am I using completely the wrong tool for the job?

TIA,
Paul
.