I don't mean to create a ruckus, but I think "Kind of Blue" is a bad choice for an "entry point" to jazz.
It's a great record, of course, but it's one of several of Miles Davis' reactions to jazz as it was at the time. It's his idiocentric statement on where he intended to go as an artist and as such it just isn't a good representation of the music for someone just getting started.
I really think that bebop is the place to start, and I'd say that something like the Max Roach/Clifford Brown Quintet recordings would be much more suitable than "Kind of Blue."
The point is to get used to the genre by soaking up the music on the recordings that best represent bebop in its formative stages, and since bebop is the defining concept of most modern jazz I think it's best to look at players like early Sonny Rollins, Cannonball Adderley, even early Coltrane records (this is all off the top of my head) where the structures and changes were still very much in the swing/functional harmony/AABA context.
The nuts and bolts of modern jazz are well represented by many records that are easy to acquire, and once all that's been assimilated then by all means move on to "Kind of Blue," "A Love Supreme" and all the later phases of jazz.
But first, get the old "rhythm changes" into your ears and under your hands and feet. That is, after all, how the masters did it.
And now you may all commence beating me about the head.