I'm so disappointed in Obelisk!
Rocky at best, it works only occasionally and is frequently inclined to simply stop the music in the middle as though it needs to adjust to a new command. (Sounds like an awesome party, doesn't it?) Further, it won't take songs directly from iTunes so playing from playlists are difficult requiring futzing with the library files or duplicating songs and it refuses to delete the songs so you can start from scratch. At the end of the day it does little more than overlap songs which you can do with iTunes anyway.
Oh, where, oh, where is the great DJaying software the works smoothly with iTunes?! Well, look much further, cuz Obelisk ain't it.