Progressive Philippines,
I understand your point and thats why believe someone knowledgeable in tone should be considered more authoratative than some stranger and thats why you should listen again. However, the danger of not realizing that your tone is bad is that there might be something wrong with your standard. As an extreme example, if you grew up on Lumanog guitars and it was fine with you. Then someone comes along and says that it sounds bad because he uses Martin. You go back and say, "It still sounds good to me" but not knowing what a Martin sounds like. You now shut yourself to the possibility of using a Martin.
In my case, I discovered tone because people have put me and my gear down. As I narrated in previous posts, the first time that I was in this similar situation was when my worst sounding guitar a Floral White Ibanez JEM VWH with vine inlays was beat by Arie's strat. Point by point Arie showed me what was wrong with it. From wood warp to actual problems with the sound to response, to playability and to character. It was clearly a badly made instrument that did not sound good. I felt let down by Steve Vai. That day was the day that I started to learn what a good sounding guitar should be.