What kind of time horizon do you want? I just bought my first headphone in about 4 years ($50 zero x crin iem) but just to use at work. Based on what I've listened to it's not worth upgrading my main setup until I decide it's worth a stax 007mk2 or I need different features (rme dac with it's in-built EQ)

To me, my stax l300 limited are peak audio. My lcd2c are source-forgiving and sound good everywhere. My 58x fill the same gap. Audeze isine20 with BT for basically a lcd2 on the go, and a massdrop+ for isolation.

I previously was happy with my hd580/hd650 for a long time until disposable income and my curiosity of different driver types caught my interest. A $200 58xj and a $50 zero x crin would probably satisfy me if I didn't already buy the rest