It's true, Allan HOLDSWORTH is the crasiest motherf... to ever touch a guitar... But he isn't the easiest door to enter jazz.
I'd say listen to guys coming from rock background, like Robben FORD, Mike STERN, and work it up from there. The first Jazz CD I bought was "chops" by Joe Pass and Niels Orsden Petersen (can spell his name) and I thought they kept playing off key, but now, it sounds amazing.

Your ears need to be used to hearing that kind of complex harmony. Then, when you are used to it, move towards Allan HOLDSWORTH and other guys like that...