ahh i remember when i first found jazz... really found it, probably also with Kind of Blue, which is in my opinion probably THE most accessable jazz album of ..well our generation perhaps.
Don't let these "jazz" folk lead you astray (thats right, follow my opinion) you'll overload if you go for Love Supreme (as you found) and Bitches Brew right away. hell, I can't even listen to bitches brew unless i'm in the right mood.
Also, forget birth of the cool (for now)... and i don't want to say forget blue train (so good) but i'd say go for giant steps first. its that pure sound that we all want to call cool, but its really the modal feel [of Kind of Blue] that really captures us, and IMHO the "sheets of sound" in giant steps is a great compliment to it... i belive that trane had recording sessions for kind of blue and giant steps in the same day (even though the giant steps release was delayed) hard to believe, given the difference in style. point is it captures that same pure sound that is unbeaten (but not unmatched) in Kind of Blue.
I have to cut now and agree with an earlier post mentioning bill evans trio. forget your ordered list, go out and get Bill Evans Trio "Sunday at the Village Vanguard" right now. I won't try to explain it but just say I listened to this album every night before I went to sleep for ...about 6 months, and it's still magic every time I hear it. be careful though, without scott lafaro who sadly died 10 days after this concert was recorded, his trio music never sounded the same... (for future reference)
Next for davis is not his big production Gil Evans productions... they sell but... not the same magic you're looking for. I recommend ESP for that great modal sound that leaves you lost in space, which was the first of his new 60's quintet, so no more trane, but don't underestimate wayne shorter (the new horn man) And with Trane don't forget "Seven Steps to Heaven" "Milestones" <-- the introduction of modal to jazz and "Someday my Prince Will Come" which all surround that same blue feel. Milestones is perhaps a little brighter, but regarded probably in higher respect historically than kind of blue itself.
I'm making this unreadably long again. but I must continue. I love Herbie's 60's stuff, but they're simply not as catchy as davis', so put those off 'til later. Jazz listening takes some working up to, so once you're ready you can move onto guys like the jazz messengers and thelonious monk on the early side and bitches brew (but start with "in a silent way" if you want to listen to fusion, its brilliant) on the late side.
remember:
Sunday at the Village Vanguard
Giant Steps
Esp...
"time out" was a great suggestion... very very cool sound
then go for anything by any of these guys released from '55 to '65, and they started a lot of crazy stuff in this time period... but by the time you get through it you won't need any advice anymore
oh and just reading through... miles may not have had dizzy's chops but lets remember that he frontlined almost 3 decades (and not some foofy decades) of new styles, so i'd say his sound developed perhaps a bit