Once upon a time, I didn't care about sound quality. I was buying 10€ earphones at some random tech store, used them until they broke, and then bought a new pair of the same. They provided me with music, which quality was the only quality I knew of. And so I enjoyed life, happily listening to music.
At some point, I started to become a bit more serious about music quality. I started with a pair of entry-level headphones from a reputed brand, and when they broke, switched to even better quality (both in terms of sound and robustness). Once I was used to my new shiny headphones, I remember retrying my old cheap headphones as an experiment. The quality was so insanely bad, I couldn't even understand how I could have been listening to this kind of material for so many years. My new headphones were so much better. And so I enjoyed life, happily listening to music.
The point of this story is that it seems there is no difference in terms of contentment between both eras (cheap headphones, good headphones). In both cases, I enjoyed life, happily listening to music. The only difference is that the contentment of the good-headphones-era relies on something that is more costly, and overall more complex. More complex because having access to decent sound quality gives you access to nuances you didn't notice before (does the sound profile favor bass or highs? etc), and requires everything else (your audio source, sound card, the recording itself, etc) to be up to this quality. So, apparently, the only thing I've done is increasing the complexity of my contentment. This sounds like a bad thing.
Of course, there is something else that has increased. That would be what we could call the sophistication of my contentment. Or maybe the expansion of my mind. Basically, the concept that underlines the fact that I have now access to more details in the music I'm listening to, and more generally to a better experience. Would have I ever really enjoyed Pink Floyd's Comfortably Numb's guitar solo as much as I can enjoy it today if I had stuck to my cheap headphones? Probably not.
So, if we assume that there is inherent value in expanding the sophistication of our contentment in order to live richer experiences, we are facing a trade-off: the more expanded our mind, the more complex our contentment, the harder it is to maintain, and the more painful is the risk of losing it.
An example in which the trade-off is certainly not worth it is drugs. Some drugs allegedly gives you access to an expansion of the mind one cannot even fathom without having tried it. But they lead to a contentment that is so insanely complex (costly, terrible hangovers, dangerous for health, risk of addiction, risk of overdose, etc) that the contentment will eventually disappear when it starts being crushed by the weight of the complexity. (In comparison, good headphones look like a really good deal for mind expansion!)
Curiously enough, I can't find a reverse example where being content of something too simple would be lacking in terms of expansion of the mind. Maybe I'm just not imaginative enough, or maybe it just says something deeper about the trade-off: if being content is inherently more valuable than being sophisticated, then good answers to the trade-off will be skewed towards simplicity.
One application I can find from this insight, is that maybe we should slow down work and produce/consume less stuff, which only purpose is to obscenely complexify our contentment. That would let us have more time to enjoy the simple things.