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.
I can now dial an extension #, and get a line out. I'm pretty happy with how it is working. Next step is to figure out attended transfer and the conf button on my Grandstream GXP2000
That worked out of the box in Trixbox, but I ccan only blind transfer in *NOW.