So this approach should be tempered with common sense and personal interest. To my mind, the transcription of songs is the most valuable area to pursue. I used to hang with piano players a lot because they usually had the best changes and new hip voicings. In order to transcribe a song, you need to get the melody and the harmony and precise rhythms. If it is an arrangement, then that adds another dimension.
Every tune contains it's own lessons and many jazz compositions are unique unto themselves.
This is always the best way to learn a tune and keep it for posterity. In each case, Miles took extreme liberties with the songs and ended up confusing generations of players. It is always best to go back to the original recordings, again particularly with Monk who recorded later versions of his own tunes differently. The original versions contain the original vision and inspiration. For a long period of time, I worked as a professional transcriptionist doing lead sheets for Joe Henderson, McCoy Tyner and, in particular, Herbie Hancock.