I can answer you secondhand as co-admin of a media server, but I do not have direct physical contact with it (I access it via RDP).
The shows to be streamed are in a single "stream" folder by artist and follow the LMA naming convention (e.g. gd1972.mic_info.mp3f)
Each show has a playlist generated for it and a "last song" which is a segue to the next show to be played (kind of a PSA announcement).
The shows queued for processing (to the "stream" folder) are kept in a separate folder with text files, etc. until they are processed.
The entire show database is on SQL 2005 and reports to a web page what is playing, and what is queued up next ~ this can be seen at
www.biscoradio.com.