Echoing what others have already said, but this is a very nice post man. Thanks for sharing.I doubt that most musicians would gravitate to a particular genre because it's easier to play than the one they really wanted to be involved in. And a "failed jazzer" is someone who just didn't put in the work and push themselves hard enough. If you want something bad enough, you're going to do whatever is necessary to get there.
Comparing jazz to prog is like comparing apples to oranges. Improvisation is the main ingredient of jazz while composition is at the center of prog, but the lines can and will blur. Some of King Crimson's music had more to do with improv that composition and some jazz artists' albums like Wayne Shorter's "Atlantis" is more about through composed pieces than improvisation.
I'm 64 years old and I'm glad that I came of age when I did; there was great groundbreaking music coming from a multitude of genres in the mid '60s through the mid '70s. Music wasn't segregated the way it is today and you could hear various styles on the same radio station. I was excited about so much of it and still am! I became a musician because of The Beatles, but my musical journey lead me to places far from pop. And lots of musicians from my generation are the same as me; they're into (and can play and write within) several different genres. I gravitate towards jazz as a player because I prefer to improvise over richer and more harmonically challenging chord progressions than most rock (and even prog) has to offer, but my composing has been something closer to prog/fusion than jazz, because... well, I don't even know why; maybe I just don't hear a bunch of ii/V sequences when I'm writing. One of my all time favorite bands is Bruford; for me they had the perfect balance of composition and improvisation.
Anyway (and before I ramble too much), it's not about what's easier and harder; it's about where your passion lies and how driven you are to be able to do what you love. I'm not so into genre categorization; for me, there's only music that I like/love and music that I dislike/hate. I play the latter often to make a living, but I stay involved in the former to keep my integrity and sanity.
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