I always found it frustrating to argue about *whether* a song might work, when it's almost always quicker to just learn the song and try it.
Do you have a website where fans can request songs? You could also ask your regulars for feedback on songbook choices.
I don't know what kind of person, or musician you are, but here's something.
I get this obsession over a song sometimes, where I just really WANT to do it. Where I say, "we have four sets of material, and we can play all kinds of songs based on being popular, or 'dancy,' or whatever, so we can always have ONE song that we just LIKE TO PLAY."
But the obsession is more than that. The song gets under my skin. I hear each part of the song in my mind constantly. The bass line. The drum parts. The guitar parts. The lead vocal. Every single nuance, and it plays over and over in my mind, and I don't want it to stop.
I want to know, CAN I PULL IT OFF??? Can I make it my own? Can I give a great performance, and take three, four, or even five minutes of my life, and make it have some meaning?
And then the talk of whether it will go over stops sounding like anything more than meaningless chatter.
I'll give you a great example of how the wisdom of "what will go over" works.
We have set three set up to be the most "dancy" of all the sets. Two Prince songs. "Use Me" by Bill Withers. "Always on the Run" by Lenny Kravitz.
90% of the time, that set is MONEY for getting dancers out, and people love it.
On the night it was pretty dead, the few people we did have HATED that set, and asked us if we played any "real rock and roll."
One guy was about to become difficult, and then we played "Voodoo Child (slight return,)" and he was mesmerized by it, and said we were the greatest band he had ever heard.
So yeah, you can overthink this stuff.
I want to sing blues songs because they cleanse my soul, and express my pain, and passion.
Why is that so hard for people to understand??
This is a business?
I get up to a thousand dollars for shooting a wedding.
I'm lucky if I walk away from a particularly good show with $200.00 in my pocket, and that's NOT including expenses.
Business, my ass.
I play for fun and exposure. I put my best effort into entertaining the audience, because that's what we're there for.
And the best way I can do that is to play good music, and play it well.