Steve,
You're 100% correct about the repertoire. That's a performers duty - to know the pop stuff that the crowd enjoys. WE all have our little "specialty" and I'm sure NO one has all the answers, but this much I know:
Play where the crowd is on your side! Remember the Blues Bros. movie? If you need the chicken wire for protection, you're playing the wrong rooms.
I has been so very fortunate all these years to find places that cater to the age group that likes the music I WANT to play, so there is not much that doesn't work, but weddings, Bar Mitzbah's etc..... that's where you earn your keep!
New tunes are a MUST HAVE! As soon as we get complacent....we get replaced.