Who's winning?

Depends. The 30k speaker might be bringing in a larger amount of pleasure than the soundbar person, but the audiophile still sees a way to improve it. 

To use the classic example:

"It is better to be a human being dissatisfied than a pig satisfied; better to be Socrates dissatisfied than a fool satisfied. And if the fool, or the pig, are a different opinion, it is because they only know their own side of the question."
John Stuart Mill, Utilitarianism (1863)

So what do you think, OP? Would you the pig/fool or the human being/Socrates?

In my philosophy, the person who is totally enjoying an experience is 'winning' over somebody who is not. Might not even be 'winning' or 'losing', just 'different'. 

While I don't understand churners the few I've known seem to be happy living in the churn so whom am I to judge.

And for those who understand about the downsides of desire there is more to. it than winning and losing.

i see a Pareto optimal frontier where they both are winners

cue Peter Gabriel

It depends.  Perhaps the person who spent $30K on speakers can replace them with $40K speakers with less inconvenience than the other guy can upgrade his soundbar.