There's a lot of good advice in this thread. Joining a local audio group and listening to many systems in real homes is among the best thing mentioned, if that's an option for you.
You can't assume that everyone who has owned many pieces is a flipper and discount their statements/opinions without more context. The financial limitations and other inputs (e.g. relocated from a big house to an apartment) result in many zigzigs even if "flipping to the latest" isn't part of the equation. System synergy is real, and as we moved towards more "rolls of the dice", more bad fits are inevitable. For some, buying used is a long home demo...not the worst idea.
Some of the best advice I've heard is to make an upgrade only if you're confident that it will be SIGNIFCANT. Often that comes at a high cost. So for most of us, that translates to infrequent, but bigger steps.
There's really no wrong answer, but those of us who flip less do free up gray matter for musical discovery, awareness and joy. @reubent @tomic601 @big_greg and I spend more of our time on the Gon sharing musical suggestions, enthusiasm and learning in a thread that's been spinning at a steady 33.3 since 2004. IMHO, when your attention drifts similarly vs. "latest/greatest gear", you're on a good path. Cheers,
Spencer