Not very much to add here after all of these jazz monsters chime in but the OP asked about painless fingerings. Joe Pass once stated that he did not play any difficult to make chords. He tended to use that he could easily reach with his hands. His reason was that if he worked really hard to learn to play this chord that twisted his hand into shape requiring more than usual stretching etc., he would loose that much time being present with the music. His goal was to be very present with the music and respond to what was going on in the music. With that said Here is one of my favorite ways of playing Am7b5/D7(b9)/Gm.
556(Am7b5)/546(D7b9)/355(Gm).
Talk about painless.
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