Oddly enough, I view contemporary popular music with boredom too.
I'm one of those musicians who plays jazz. I'm a double bassist and a so called "day jobber," meaning that music is not my primary income source. Am I an expert technician? Sure. A decade of classical lessons, thousands of hours of practice, and 30+ years on the bandstand will do that to you.
Why jazz? Well, for one thing, contemporary popular music doesn't even involve my instrument. I'm obsolete. ;-) And I love the double bass -- the sound, technique, history, contemporary leaders, and even just the sheer absurdity of it. For another, I've developed my jazz chops to the point where my best chance of making further musical progress is to continue with jazz. I don't know where I'd even begin to come up with new ideas in the contemporary pop styles, or how I would turn it into a performance art.
There are a couple more things. While there's certainly a market for contemporary pop music, it's utterly saturated with talent. And pop music has always been youth and appearance oriented. As to how credible a 52 year old guy would be in that scene, I'll leave to the imagination. And the target demographic has been conditioned to expect entertainment to be free. For a non-superstar, the popular scene -- even going back as far as rock & roll, is depressing.
So a few of us who have no prospects in popular music, but enjoy performing with some semblance of dignity, will be drawn to other musical genres. In your locale it may be jazz, but more broadly it's also classical, baroque, fiddle music, accompanying dance clubs, etc. Living near Chicago, there's a lot of blues. Players who are still interested in the electric guitar & bass find outlets in the various forms of heavy metal and rock music, playing small venues that support original music.
Money? Surprisingly, yes. For almost a couple decades, I've had a pretty consistent schedule, of roughly one gig per week. Most of the work is paid, with very little overhead. There's no heavy equipment to set up, and commercial gigs such as weddings and corporate events are un-rehearsed. I've never had to go on tour. At the same time, rock bands find it almost prohibitive to break into paid work, because the established players tend to corner the market on the good commercial work.
Another surprise is that an audience will crawl out of the woodwork when good music is being performed. Not a huge audience, and not necessarily a drinking audience, which severely limits the economics. But people will come. Some are musically omnivorous, or even like newer styles, but show up because we still know how to entertain, and we can perform without driving you to deafness.
So I'll never claim to understand the economics of the music business, but it seems to me that there are little niches where people can enjoy performing with dignity while opting out of the mainstream popular music scene.
My kids, both teenagers, have shown no interest in either jazz or popular music, as musicians. They both prefer classical.