I, too, have troubled over what songs to keep in the set list and what songs to drop. I've never counted how many songs i know but it is definitely in the hundreds. And Even though i am over 50 I don't have much trouble learning new songs. I mostly sing the new ones over and over again in the car when i am traveling until i have the words and phrasing and breathing worked out. The chords and rifts are easy (as Rick says) because i like the song enough to play it at home a lot or i wouldn't be learning it. What i constantly wonder about is the audience. There are certain songs that always seem to draw a response from the audience i.e. applauding when i start the song or the audience singing along right from the beginning or more motion (dance like). It seems to be true no matter how many times I play the same songs at the same venue. So I keep playing them in the set and fortunately I like doing them. Other songs come and go depending upon how i feel on any particular day or how the audience is responding. If the crowd is subdued i tend to do more up tempo livelier songs trying to keep my spirits up as well as to enliven the crowd. If the crowd is more attentive i like to do some slower more musically complicated numbers. And I always do songs to sing along with if the crowd is responding to audience participation. But, Les, I am constantly wondering how often to change the set lists. Does the crowd want the same old songs? (like they do if it is a record hit as mentioned by Hank) or do they want to hear new stuff? (i.e.how many of my own songs do i play?) This question is one of those constant worries that i have never satisfactorily settled in my own mind. Thanks for bringing it up. I hope we get some response to this thread that helps us all.