I find it DOES make me happy.
As I have gone up the upgrade path, each step has given further improvement and knowing that there is yet more to come gives something to strive for.
I truly enjoy listening to music on my current system - and am about to do a major upgrade to amp & speakers, due to some money I have coming to me. I was getting VERY frustrated doing the rounds to demo kit from other manufacturers in case something would give me an improvement over a step up from my current brands - but much of the stuff I heard, despite costing more, was far less enjoyable than my existing kit - that surprised me and the frustration built ..... and built .... until I decided to simply try stuff higher up the range in what I have ... and WOW - now I'm happy again to know that past decisions have been wise and the upgrade will allow EVEN more of the type of sound I love.
The pleasure comes now, from listening to what I have. I have even considered the fact that it's not worth upgrading, because I do enjoy the current kit ..... but now having heard stuff higher up the ranges, I know there is more to attain. If the funds were not there, I could still enjoy what I have - which is reassuring.
How can desire be an enemy?? ..... when it gives you a purpose and something to strive for. Everyone has desire for SOMETHING in life, otherwise there would be nothing to get up for in the morning.
If you struggle to enjoy listening to the music, it could be that you have not purchased wisely enough within whatever budget you have....... as I mentioned, I have heard kit recently, costing far more, that gave me less enjoyment.
...... OR - it could be that your budget does not meet your expectations - and that would be truly frustrating, I imagine.
if you heard pretty much all combinations of kit in your price range and were still unhappy, so 'for fun' auditioned kit at a higher level and found something you loved, but couldn't afford ... arrrrrgh - nightmare!! Especially if life did not show you a way to attain that at some point.
I guess it has to do with the point where the law of diminishing returns kicks in enough to make further investment in this hobby too costly. If you are still unhappy with the sound at that point, I can only imagine that the search needs to be widened on what you have heard at your budget.
Plenty of people are happy with their budget separates for a £500 system and cannot see the need to spend more .... yet on hearing a £2000 system could be blown away ....... if they were to hear one.
Likewise, those in that bracket might feel the same about a £5k system ......... and those may feel the same with a £10k system .....
Belief systems may dictate whether they can justify the spend, if they have the funds ........... and also whether they even bother going to listen at all, at a higher level. A couple of friends of mine cannot believe what my system costs, or what I may spend next, thinking that their £1000 system is SO good, that how can it be worth spending more.
a) I envy them in a way - that they are happy at that price point .....
b) I pity them, that they may never enjoy something slightly more high-end on a regular basis
May the debate continue!!