dsper, many of the newer artists and recordings suggested here may be good jazz, but they are not "more of the same" as your Cannonball album.
The "closest" was already suggested, the ubiquitous "Kind of Blue". Other similar recordings will be the Prestige albums by Miles --
Similarly, the "Bags Groove" recording with Milt Jackson and other period stars is worth a listen.
Regarding analog playback, I don't believe $4-5K is necessary for a decent system. Your KAB modified Technics is a good foundation. Adding a new Grado, Audio-Technica, etc. cartridge (MM can be fine), carefully set up, with a decent phono unit and you should be set. Except a good record cleaning device should also be added. There you can spend a couple of hundred or thousands.