Yea, there's a plethora of shoutbox plugins available for vBulletin.
The downside is that most shoutboxes don't refresh automatically (except the AJAX based ones), so we might not be able to find a good one. It'll be worth looking into though, as it can be a viable alternative.
The War Room sounds nice!
Some chat plugins have the ability to report users, so that it can be monitored indirectly. Design work won't be a big deal, as that's included in the plugin's package. The chat will probably end up on a separate page, or if it's a shoutbox right above the forum.
Only if we manually build it in, it'll be a lot of work, but I believe that also causes Kc to lose the official support from the vB team that's included in the license. So I don't think that'll happen anyway.
Don't quote me on the license thing by the way, as I'm not entirely sure about that. It's just what I recall from another place
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