with playlists i'm just dropping files in place and listing to the end and beginning of each and how they fit. When I'm DJing I'm just going with the flow 95% of the time... might be because I'm listening to the songs all the way through so I have a clearer picture of what should come next. How the crowd is responding is a major factor too... no reason to stick to a set list that isn't moving the crowd.
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Reunion Radio Podcasts
Bringing Together Five Decades of R&B/Funk/Soul/Dance

http://reunionradio.blogspot.com/