What you’re describing is a 3k new release which depreciates to 50% of MSRP in 1-2 years max and then there is a brand new super enticing successor for 3-4k and you’re wondering if you should upgrade…That’s just the name of the game in this hobby, wherever you live…
In general, there are a few ways to deal with this, depending on the size of the wallet and levels of madness:
1. Large wallet: do whatever you want, YOLO.
2. Medium wallet / smart: buy new releases with a (review) discount, enjoy them for 2 months, and then sell with limited or no loss
3. Medium wallet / less smart: wait for 6-12 months after release and then buy it used for 30-40% off. Keep for a year and then sell with a relatively small loss.
4. Medium wallet / dumb: same as nr. 3 but keep them forever, letting them depreciate to zero. (My strategy …)
5. Small wallet / dumb: buy new like you can afford it …
6. Small wallet / smarter: buy one good IEM in the used market and stick with it forever
7. Small wallet / smart: delete your headfi account now