I would be surprised to see Rich provide comics to the online Dragon. First, he sort of made clear his unhappiness at them canceling the print Dragon in the last three OOTS he did for Dragon, where he pictured, among other things, a wizard of the coast bowing down in worship to a Mr. Potato-Head.
Plus, I think putting his comic onto another website other than his own is just competing with himself. He would want people who were online to come to his site, not WotC's. The print magazine was different, because it was a separate medium. People who may not have been online-savvy could buy it at the newsstand. But most people who are online and play D&D have already heard of OOTS, I think.
And personally, I hope he doesn't do it, because it will mean even MORE delays for the free OOTS strip, and I don't intend to subscribe to DDI anyway!