I don't like really expensive wine. I feel like a lot of the time it tastes like wine with a bunch of gravel in it. I really don't like expensive coffee. It's too bitter. I've listened to some five and low six figure sound systems and while they seem impressive they seem like they're trying too hard I can also find the sound kind of uncompromising and the whole experience just overbearing.
Mostly, expensive systems are an aesthetic that's harder to achieve at a lower price point. The fact that it's hard to achieve that aesthetic at a lower price point doesn't mean that it's somehow better. I've watched a lot of people chug down expensive wine without knowing if they liked it.
At some level there's a lot of diminishing return chasing some imagined super system. The whole hobby is filled with confirmation bias, and desire for desires sake, and if you ask me, a lot of junk science.
My main system is a Tom McNally SET amp that I bought for $350 in a Harbor Freight parking lot and a pair of Omega speakers which are single drivers. I love that system and wouldn't trade it for anything. It's easy to listen to for extended sessions and the mids sound great to my wife and I.
In the end, you'll be happy with your system when you allow yourself that pleasure.
Ultimately there is no objective measure, not really, as I don't listen to test tones in an anechoic chamber.