Back in the days when I sang on the street, I rarely "moved along" once situated in a good spot ~ and I would stay at it for 6, 8, even 10 hours on a good weekend day.

Repeating oneself, even as often as hourly, is hardly an issue. The listeners are constantly in flux. If someone indeed has stayed to listen to you for an hour or more, they undoubtedly like you so much that they probably wouldn't mind a reprise or two.

I was constantly expanding my working repertoire, not out of fear that the "audience" wouldn't stand for any repetition. but simply for my own amusement and to fend off boredom. Still, if I really enjoyed a given song (especially one I had only recently learned), I wouldn't hesitiate to play it in "heavy rotation."