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Yes, after posting I realized that self-mixing creates a mostly-self-connected sub-graph. You really need to start with multiple transactions in, ideally randomly occuring during the mixing process, and not spend all your bitcoins at once.
Somebody who knows a lot more about graph theory, statistics, and probability than I do should chime in and tell me how I'm wrong or come up with a good metric for the ideal amount of mixing (I bet too much is just as bad as too little). Analyzing the connectedness of the existing bitcoin transaction graph might be a good place to start.