Some thoughts popped into my head while reading the article and I should have written them down but the few that remain I’ll chime in with now.
When you wrote the “outlines of what you want” my mind immediately went to an outline of an image versus the outline of a written paper or presentation. I’m a visual thinker which is weird given that sound has such an impact on me emotionally when I sit down to listen (not critically) deeply. I even thought about the why I limit my critical listen outside of the boundaries of my deep listening.
I thing everyone has a place in the audiophile spectrum and I think my place falls between you two in that I share that need for wanting it all perfection and the need for the tinkering and mixing and matching. I also share you limitation of space as one of the factors I can’t overcome so I’m simply learned to embrace the shortcoming.
Often when I go to a show the “size” of the room screams out at me how grand things sound. That said, I’ve never yet come back from a show and not loved the gear I’ve chained together when I go back and try to remember what I heard and compare it to what I’m hearing at home. That’s obviously the room and the fact that I’ve spent so much on perfecting it to my taste.
Getting back to your outline comment though, I think for me it’s something that happened organically and for some reason or another I quantify a system more on how it makes me feel rather than it’s sound. I’ve taken some pieces in a direction that have genuinely floored me on their detail but yet I didn’t enjoy the music I was hearing from it. There are some situation where you like what you’re hearing and you know you can tweak it enough to get to what you want and there are others that you simply know it’s not for you.
I can’t agree more about experience being the key and this is a solitary hobby by nature and chasing that experience is something that you have to work on. Either going to shows or more meaningfully listening to other people’s systems. A show is never going to be what you get at home, it’s merely a hint and it can go the wrong way once you get it at home. A friend’s system on the other hand is something they’ve put together, curated, shaped and hopefully gotten it to a place where they’re content.
That content is what I like to refer to more than end game. I say this only when I reached a place (with my 2 ch) where I no longer thing about what I’m going to change on it, or how to make it better and there’s no more end game than that.
The way to get there is simply as yourself what is the system not currently giving you and then research avenues, cabling, gear, power, room treatment, whatever; as a way to get there. But you know you’re there when the thoughts no longer hit you or when you know that you’re simply unwilling to take the next step because of the limitations. Whether they be room size or budget or whatever. What I call a rationed content. 
Look forward to your second part. What’s the ETA on the amp anyway?
One last thought, that I’ll share. I’ve scratched the desire to take things to the nth degree by simply addressing to 100% every, and I mean every aspect of the audio chain. Footers, platforms, cabling, ground, power, room treatment. If I felt it could improve on the sound, I have addressed it. It’s funny but when I add up the cost of my system, I only include the components, but I probably could buy a nice used car with the amount of money I’ve plunked into “accessories”. It’s no wonder why I don’t add it up.