[Mr. Jelly]

Originally Posted by Mandobart

People are always asking this, with good reason. Your best move is to go to the venues you want to play as a listener and observer. You'll see and hear what works with those audiences

This is the best idea really. Other factors not mentioned are that the ground work has already been done for you. Songs that others play live usually have been vetted for being fairly easily played live and the audience has been conditioned to receive them favorably. Be careful not to put to much weight into older entertainers as you may be trading your old material for theirs.