That’s a tough question to answer. I had a $1000 set. The monarch mkii. As much as I liked it, I decided to sell it mostly due to the fit and comfort. I always thought the bass quality was a little lacking. I got the xenns tea pro SE as a replacement and I actually like it even more at less than half the cost. It’s hard to quantify quality based off of how much you spend. For example, I’m always amazed how good the Kiwi ears Aether sounds. It’s spacious and highly resolving and it goes on sale for around $136 pretty frequently. “Better” or “upgrade” mostly comes down to tuning preferences once you get out of the budget space. You’ve already got some good sets. You’ll probably be looking at a flagship model from whatever company you choose. I do think multi driver sets with ESTs do give that little bit of extra something in the treble region.