Here's my experience. I don't expect yours to be similar, but I feel strongly about what underlies a compulsion to tweaking. Srwooten, you said in your system description, "I have been putting my kit together for approximately 7 years making many changes as my listening and finances improved." You may feel satisfied, but I can certainly see why your boy would consider you to be dissatisfied if he sees a parade of equipment over time and his dad hovering over the rig trying to coax more out of it. A kid knows when he's not happy about a toy and he tries to futz with it to make it more enjoyable; he's seeing the same behavior in you. :)
I have had habitual gamblers tell me, "It's not about trying to get rich, it's entertainment..." Delusion comes in all forms. It's very similar to the audiophile who tweaks incessantly saying, "I'm satisfied..." I believe discontent is at the heart of both habits.
I used to tweak constantly, and it was because of periodic dissatisfaction with the sound. I see no other reason why anyone would have to "toy" with a rig. Doing so for curiosity's sake? Maybe, but behind that action is the hope that something good will result. Having a principle of "Always onward and upward," in terms of performance? A recipe for regular dissatisfaction.
The primary reason I tweaked was in hope that somehow I could get an above average outcome in sound from an economical adjustment to the system. Experience taught that it's not possible. You have to pony up the money to get the right components to get the dream sound you want. Only when I invested enough in the rig to elevate the performance way above any potentiality from tweaking did I largely give it up.
I do not consider working with cables, a component, to be tweaking. I still spend time on matching and trying cables for different influences to the rig. But if I'm not happy enough to enjoy a rig without sticking blocks under things or weights atop of speakers, etc. then it's time for a major change, not a minor one.
I found that tweaking KEPT me from making big advancements in the sound quality. It had me valuing puny, nearly insignificant changes to sound quality, rather than seeking out vast, huge differences. I was deluded by thinking that I had reached nearly the pinnacle of sound quality. What a joke. There were many levels of BIG improvements to be had, and I was farting around with stupid little adjustments which did virtually nothing. Once I realized that the real game is in the component selection and integration that was about it for tweaking. And for the whole game of fostering periodic discontent with the rig.
It's one reason why I don't spend much time reviewing tweaks. My view is that they actually trap a person into a limited view of what's possible in building a system! I'm sure there will be some who will strongly disagree, saying that tweaks yield huge results. I did not find that to be the case, and I would much rather put my money on a component, cable or speaker change than piddly adjustments. :)
Meanwhile, through the years it became evident that I was not going to be satisfied with one speaker, no matter how high the quality. I have a desire to hear different technologies, and thus radically different presentations of the music. No amount of tweaking could resolve that perceived need. I'm glad I figured that one out, because my satisfaction level is worlds higher than when I was tweaking!