It mathematically makes sense to argue for a law of diminishing returns in terms of innovation and originality in art, (there is plenty of not real tasty supporting evidence around). But occasionally surprises have popped up and have appeared to breathe new life into a dead horse... it's hard to say that will never happen again.
Anyway, the O.P. list indicates that there is A LOT of potentially rewarding stuff for him to check out. How someone gets to a point where they dig music that pushed or is still pushing boundaries can vary quite a bit. It's not hard to see someone maybe picking up the 1st Friends of Dean Martinez disc...then getting Michael Hedges Aerial Boundaries or John Abercrombie Timeless and moving to Zappa Grand Wazoo or T.J. Kirk... and after that stuff like Mingus, post 60's Miles, Can, Monk, Terje Rypdal, Mahavishnu Orchestra, Ornette Coleman, John Zorn, King Crimson and Stravinsky.
Anyway, the O.P. list indicates that there is A LOT of potentially rewarding stuff for him to check out. How someone gets to a point where they dig music that pushed or is still pushing boundaries can vary quite a bit. It's not hard to see someone maybe picking up the 1st Friends of Dean Martinez disc...then getting Michael Hedges Aerial Boundaries or John Abercrombie Timeless and moving to Zappa Grand Wazoo or T.J. Kirk... and after that stuff like Mingus, post 60's Miles, Can, Monk, Terje Rypdal, Mahavishnu Orchestra, Ornette Coleman, John Zorn, King Crimson and Stravinsky.