I know there are a few playlist users around, some requiring fairly complex multi track setups with midi. In searching for a future live performance backing track solution (outside of the glorious return of Sonar!) I was drawn to Abelton live, but did not like the fact that you had to load all of the show tracks into a single project. Clunky much! I have come accross a solution however and am keen to give it a run. Obviously it is still a #@#@load of work changing projects over, but at least an individual project, automated, remote controlled playlist looks possible in Ableton Live - using "Midi Automater".
Check it out if you are interested:)
http://midi-automator.com/?q=node/11 EDIT- and if I am not mistaken this will work with any DAW.