We have deployed the chat on the live site, but there were some changes we had to make from our original plan. We found that loading the JS on every page was just not going to work, it was taking too long for the browser to process the JS each time. We played with different ways of speeding this up, but even as we got the download to be as quick as we could, it was the processing of the JS that held us up.
We decided to go another route that would give the same functionality, but not require the repeated downloads on each page. What we came up with was to use an iframe to anchor the chat to the bottom of the page and then load the rest of the site above it. It worked like a charm, and the only downside is that it will be hard for people to bookmark pages when the chat is activated. We made the chat something a member had to start, and then also added a "quit chat" button that gets them out of the iframe.
The contacts match up with the buddy list, the login has been automated, and the chat windows alarm and keep the conversation even when the window is minimized.
Here is a screen shot of what we have. The gray bar at the bottom is the anchored bar, everything above that is running in an iframe. From this version we also got rid of the add/remove icons and just push the people to their buddy list within vbulletin to handle management of buddies. We also added the logout button at the bottom of the buddy list window.
Going to see what it will take to share this with the community to help work out more of the bugs that I'm sure are hidden in there somewhere.
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