After quickly (A few days to a few weeks each) trying out each of Trixbox CE, Trixbox Pro SE, and Asterisk NOW I have settled on Asterisk Now because it seems to run stablely on my VMWare setup, and doesn't intentionally cripple features I like.
There are a few features that I had set up on TrixboxCE that I'm having troubles with.
Tonight I concerned myself with the DISA.
I played around with it earlier this evening and managed to get it working.