The chat feature is nice for things like changing names, merging reservations, and making requests, but there are limitations to what they can do with chat. Apparently, they do not have access to availability. So, they can't do things like process a waitlist match (although they can tell you if a waitlist has matched) or tell you if there are
DVC cash rooms available for specific dates.
Like others have mentioned, if it shows as unavailable, I reload or hang around until the chat bubble appears. It seems to have been a little better lately. Maybe, I have been lucky!