"Think outside of the box" (pentatonic) and when you get lost go back to the box.
Learn different rythms, like the swing feel for be-bop
Bossanova and latin have a different feel rythyms as well.
Have patience and yes theory is a +. Good luck in conquering the Monster of Jazz.
There are several books on Guitar methods you can check out.
Mel Bay's complete Jazz guitar Method will give a structured idea.