It's an evolutionary process ... not just in terms of how your equipment choices evolve, but also how you gradually learn what type of sound appeals to you the most. Honestly, when I started I had no clue what I liked. So it's not always about the synergy but also an exercise in self-exploration.
Profound observation and eloquently put. This is the kind of discovery that puts the lie to gear-churning and rash upgrading. I can imagine one engaging in this hobby not with the goal of reaching "the top" but of listening to as many kinds of systems as possible. And the best part about that goal is that it is best done by exchanges with others -- meeting people, talking, listening, developing a vocabulary which reaches across rooms and ears and tastes. It's really what makes this a "hobby" and not just a consumeristic merry-go-around. Of course, the influencer industry on YouTube (and magazines, etc.) finds such a method anathema to their business, but that puts their opinions into proper perspective for the rest of us.