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not sure about kind of blue as a litmus test for the music as a whole.
personally, i find the record tedious, but really like the next phases of miles' output (the quintet with wayne shorter, herbie hancock, ron carter, tony williams and the first electric phase).
i am also not so sure about moving through the music in chronological order--it makes as much sense to move back and forth, following things that catch your interest--but be aware that this particular form of music built itself within/around/with reference to a tradition, so that there is much chattering between more recent music and what precedes it. but it is not as if by finding the earlier referencepoints that you will "decipher" the music--rather, it may add another level of complexity to how you hear it.
for example, you can listen to steve lacy without necessarily being steeped in monk's music--but you will hear lacy differently if you do know monk. players like lacy were not simply stuck in a circle of repetition, but used what came before as a template for moving into other spaces--when you get to someone like marsalis, things become otherwise--marsalis is interested in making jazz into something like european classical music, which i think is pretty much the death knell for it as an interesting form.
that all said, kind of blue is not a bad place to dip your feet into the pool---neither is coltrane's "impressions" or mingus's "ah um" or the duke ellington collection "the blanton-webster band" or anything on riverside that thelonius monk put out.
it is a big tradition. there are lots of great players involved with it. what matters is that you find ways to enjoy yourself as you get to know it.
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a gramophone its corrugated trumpet silver handle
spinning dog. such faithfulness it hear
it make you sick.
-kamau brathwaite
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