I regret most of my audio purchases. The first speakers I don't regret buying were Dynaudio bookshelves that I have to this day, after which I switched to studio monitors and never once looked back. Studio monitors + room correction. Can't go wrong with those. Not a week goes by that I don't catch myself thinking of how good (tight, clean, punchy, dynamic, you name it) a random song on the radio sounds and that I have never known it could sound this good. All thanks to the studio monitors.
This brings up the interesting question of how much are we looking back on our previous experience has to do with being enamoured with our current gear.
By that I mean, lots of us have been into this hobby for a long time and I’ve had different systems over the years. And generally, the reason we bought those systems had to do with being impressed with the sound and usually (at least for a period) being quite happy with it.
So the question becomes whether we can separate the quality of our subjective experiences from the more objective quality of the gear we might be using.
In other words: Does the fact we think our current gear is “ better” in someway than our older systems mean that we weren’t having really involving compelling experiences with the old stuff as well?
I absolutely swoon over the sound of my current system, and I sometimes find myself thinking “ this is the best sound I’ve heard in my room.”
But for one thing, I think there could be some recency bias operating there.
And the other thing is that the fact I am so happy with my current system doesn’t mean I wasn’t incredibly happy with the many different systems (usually different speakers) in the past.
Going all the way back to the 90s when I started off with Quad ESL 63s, I was just ecstatic with the sound and the musical experiences I was having back then.
And that was generally the case with every single new system or speaker I owned.
I frankly don’t think it’s possible in terms of subjective experience to leapfrog to some new level of joy, amazement and musical pleasure than I’ve had in the past.
My tastes have evolved somewhat over time and my current system reflects that, but in the big picture it’s more “ different” than “ better” and my overall engagement with listening to music on my system isn’t necessarily any greater than it has been in the past. (maybe it’s a little bit greater, the way my current system just seems to push all my buttons, but I’m talking big picture).