Running multiple instances of Bob is possible but probably a bad idea. By default BobEXE will find an open port to use so that it shouldn't ever have a port collision problem so if you do start it multiple times it would work but I don't think there is a benefit to it. You can host as many wikis as you want from a single Bob instance and there aren't restrictions on plugins or anything like that. And you shouldn't ever let multiple instances of Bob server the same wiki because it can very easily case strange problems.
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