My suggestion is pick out enough songs to do two full sets, right them out, tape the list, and then pick and choose which of those songs feel right in the moment. You don't have to know 100's of songs to give an interesting and new performance each time. Its also not nessicarily a bad thing to repeat some of the songs, but you want to keep it new for those repeat listeners, because they liked you enough the first time to come back... you want to make sure they like you enough the second time to want to come backthe third and forth etc.
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