Is starting playback via contact closures like the standard ones found on radio consoles something that can be done? I've used a plugin for Winamp in the past but don't see an option for Radioboss.
http://uploadgeneration.info/Winamp/www.winamp.com/plugin/com-port-winamp-control-v141/80524.html
http://uploadgeneration.info/Winamp/www.winamp.com/plugin/com-port-winamp-control-v141/80524.html