I'm on the fence with amping. I think an amp is essential for higher-end IEMs, otherwise you're wasting so much of their sonic potential. A smaller DAP is therefore ideal if portability is a must. Since I mainly listen at home, a DAP + portable amp (or a portable DAC/amp) is great for even better SQ with high-end IEMs and most headphones. A desktop DAC/amp would yield the highest possible SQ, but the lack of portability kills it for me.
Why surprised? Not only that, since many folks dump their mint 'older' IEMs for the 'latest and greatest', the old guard not only compete sonically, they can also be had for a fraction of the RRP. Even discounted, a Traillii or Jewel would cost me $1000 more than I paid for my entire Sony Signature Series system + TWS + upgrade cables.
Makes it very clear why the Cooler is such a cool place to hang out. A refreshing lack of any mention of the multitude of Chi-Fi IEMs or brands (which incidentally make up by far the largest portion of the mainstream IEM market). We're all sat in the VIP room behind two-way glass above the nightclub dance floor, yet everyone is welcome.
What a cheap-a$$ hobby we've chosen!