It took me a long time to develop an ear for more esoteric jazz. My thing is the era after jazz died, and popular music (Doors, Hendrix, Cream, etc.) became the market.
If I wanted to introduce somebody to jazz in an incremental way (there are so many different forms), I'd start with Oliver Nelson's The Blues and the Abstract Truth. It is every bit as important, in my estimation, as Kind of Blue, but doesn't get the level of accolades that the Miles record does. I'm a huge fan of anything under the rubric of "spiritual" or "soul" jazz, but a lot of those records have gotten to be collectible and expensive. There is a remaster of Dream Queen that Bernie G. cut that is cheap and allegedly from the tape- the OG is a 4 figure record- it's lo-fi lounge music, but the title track is killer. Likewise, the track "Turiya and Ramakrishna" on Alice Coltrane's Ptah, the El Daoud, is stunning. The reissue is pulled from a digitized file, the OGs command beaucoup today. If you like something fairly straightforward, try Art Pepper Today- a late record in his short life- the track Patricia, which was released three times, includes Cecil McBee, Roy Haynes and Stanley Cowell. Stunning performance, and the copy I have, an early Japanese pressing is quiet and extremely good sounding.
I tend to go for small and private label jazz that is more obscure, but it took time for me to get to this-- it is a process of learning, and being accustomed to sounds that may at first seem cacophonous. Exposure allows you to develop an ear for this- one of the least popular Pharoah Sanders' releases-- self titled, on in the India Navigation label, did not sell well at the time, but OGs now command big money. It was reissued a couple years ago.
To me, a lot of modern post-bop is a process of exploration. There's a lot of records out there. You just have to develop an ear for it and get engaged in the process of exploration. It's quite fun, though it has gotten expensive on vinyl.
