Jazz is my love and a direction I am now (almost 5 years in) just working toward, but it is the hardest discipline TMK? It's tough. 

You've no doubt hear the standing in joke, "A blues guitarist plays 3 chords in front of thousands of people, and a jazz guitarist plays thousands of chords in front of 3 people".

Without a dedicated Jazz course here TMK (?), I've a different sub source which I use heading in that direction. As it's a competitor to Guitar Tricks, I shalln't mention which here. A solid understanding of music theory is prerequisite.  

This guy on You Tube will point you in the right direction.