With the current delivered version 1.1.1 there is an issue with request.dynamic and crossfade. Only the first crossfade will be made. It will not detect the next event.
The standard package for Debian is from 2013-MAY and does not contain the bugfix. Even the standard sources are shipping the buggy code. You have to use the latest developer sources from github (http://liquidsoap.fm/download.html#latest).