Ok let me go in some more details...
The problem is not with actual streaming but with Icecast switching from AutoDJ to /live with aac+ v2 encoder and especially when you want to drop your live stream and get the /autodj source up. The error i am getting is "error syncing to stream". I need to go in and manually restart the source.
I am using winamp to stream with oddcast.
Has anyone else experience such an issue?