Joe, here's my take for whatever minimal value it might have:
I think you've hit on one of the major hurdles to all performing musicians these days. Used to be, you could learn a set of songs that could be played to any audience, but those days are long gone. As I see it, here are today's options:
1) become a DJ. I think the main reason DJs took over the wedding market is because the demographic at weddings is so varied that it would be hard to know enough songs to please everybody. A DJ can easily get a song list from clients and come prepared to play exactly what they want. If you want to perform, start by sprinkling a few performances in with the DJ songs to see how they go over.
2) Focus on the venue.
It has been my experience that live music hangouts all have their own unique crowd and music preference. Playing the wrong music for the venue is the best way to fail. Ideally, find a club or restaurant that caters to people your age, then play to that crowd (Maybe a VFW or other club type establishment whose members are typically older.) Ideally shoot for a recurring gig at places that like the music you want to play. By limiting the demands on your set list, you stand a better chance of mastering the material.
If you want to play at other venues, at least take the time to research the place and see what other musicians are playing at those locations. Failing to do so is a breach of due diligence that falls squarely on your head.
In my opinion, trying to enter the music world by throwing a bunch of spaghetti on the wall to see what sticks is an exercise in futility. The amount of work required to be ready for every type of gig is overwhelming. You'll almost certainly get discouraged and quit if you set that as your goal.
In conclusion: limit your target demographic to a set list you can master. Identify places where that group goes to hear live music, and try to form a working relationship with those places.
But be aware that it is hard to break in. As opportunities decline, the weak performers leave the business (or offer to play for free), and newbies hit the ground competing against the best performers in town, since they are the only ones who have survived. The one area where newbies can still get a foothold is private parties. Individuals hosting parties don't already have arrangements with other musicians, and most established bands don't want those gigs because they don't pay enough for a full band.
Focus on one specific goal and pursue it until you break in. Then build on your momentum. You might even want to start at your local open mic to hone your act. Best of luck...
Last edited by Pat Marr; 08/08/18 07:53 AM.