yea sometimes I think Jazz guitar doesent sound all that great. Its very theoretical and doesnt not break any rules of music, therefore it should sound good. But for some reason, I think being that orthodox is somewhat of a restriction from expressive music. Though I am a strong belive in music theory and Im on an improvising flick right now, when your always caught up in what scale should follow a progressing and always following certain rules (circle of 5ths, ect), it kinda ruins the fun. And that may be a reasons why Jazz guitar (not sax, I love all sax) sometimes sounds odd, weird, and by to book.
...I donno, alot of people may not agree cause its hard for me to explain what Im trying to say.