I have been using my Moondrop S8 for more than a year. Thankfully I still haven’t gotten the upgrade itch.

If you’re happy with your 535, you don’t need to upgrade. As for Bluetooth amps, if you want something with tons of features, check out the Qudelix 5K. Otherwise. The FiiO BTR5 is very good.

When I go for walks, I use my S8 connected to the Qudelix 5k instead of the AirPods Pro.

I myself upgraded from the Blessing 2 to the S8. IMO, the upgrade was absolutely worth it. From my experience, in terms of sheer detail retrieval, the S8 is so much better than the Blessing 2.

For headphones, I am 90% satisfied with the Edition XS. I may upgrade to the Arya V3, but not for a long while.

For IEMs, the Moondrop S8 is my endgame.

I know how you feel. Once I got my Moondrop S8, I tried many IEMs as a complement (Tanchjim Oxygen, Final E5000, Penon Serial), but I ended up using the S8 over all of them, so I am content with just the S8.

Ping pong or table tennis?

Here’s my IEM journey:

Quarks, Blessing 2, S8

Not that known, but mamomo's soundtracks are a treat to listen to on high end headphones.

For headphones, Hifiman HE400SE ($109)

For IEMs, Moondrop Chu or 7Hz Salnotes Zero ($20)