The future for Asterisk in my mind will be built upon adoption in the enterprise, not by small five to ten end point deployments. According to those close to the Asterisk community Digium is projecting this a few years down the road, but Southern California based Fonality is better poised in my mind to move in that direction.
I've long been a fan of Fonality since Chris Lyman was on a panel of mine at Internet Telephony in 2005. My view is their making the right moves in the direction that leads to a very strong enterprise offering. It's only a matter of time before something sparks the fuse and they move into that direction...I honestly think it will sooner than Digium.