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I'd start with the standards. Vocals then instrumentals.
Vocals first as a means of easing in.
Old heads first. Find a song or few you actually like then look for it's covers
I wasn't a fan of Miles either, the first CD of his I got was Bitch's Brew. I didn't like it, it was that fusion crap. Later I took a chance and bought Kind Of Blue and heard why everyone loved his music.
Enjoy
But wait, why are you working at appreciating jazz? Either you're into it or no.
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