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Speakers. Just having the right speakers for my various spaces over the years has been the biggest factor. Speakers with subwoofers has improved sound and my ability to integrate into a space. And if taken as a whole, speakers/subwoofers with DSP for room correction and crossover has made me happy beyond any other component in my system. The fact that many DSP software interfaces are pretty easy to use (even fun and informative) adds happiness.
I remember a couple of years back, when I was just about to make my first audiophile purchase. I put in a lot of time and effort to decide which to. It then when I came across the ASR forum. I pulled the trigger on Schiit Magni Heresy and AKG K712 Pro. Together they make a purchase that puts a smile on my face everyday.
The other one is Etymotic EVO. It is my daily driver.
Loudspeakers for sure. Bigger is better.
And if you have the know-how and capabilities to build them yourself you can save on A LOT of money.
I also think moving on from a very expensive Sovereign Director pre to a much less expensive Benchmark LA4 was a serious step up for me.
For me, generally speakers. But it’s not always an upgrade per se; I just like having different speakers. I don’t change much else in my system. (I’ve had my amps for instance for 20 years)
The one major exception is having upgraded my turntable 5 years ago. (And from which followed going down the vinyl rabbit hole). I can’t think of any single purchase I’ve made in many years that has given me such consistent joy.