Thanks everyone for lots of IEM suggestions!
I did a bit of research around my area and found a super nice tinkerer, who makes custom ear pieces.

And I mean custom to the bone! We had a nice chat and he is now trying to incorporate some of my left over PicoPlanet boards into the face plates. This will look super dope! 🤩

Also: turns out I have very tiny ear canals. That's why regular in-ears never had a chance.

Was also allowed to peek into the workshop, which is full of soldering stations, 3D scanners & printers and laser cutters. 🤌

He now and then posts a bit of behind the scenes stuff on his Instagram. Check him out in case you ever consider custom headphones!

https://www.instagram.com/deer_ear_iem

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Oh, when I said "custom earpieces", that was maybe a bit of an understatement. I don't only mean the ear shape cast - he fully engineers the electronics, too! It's so toinyyyyyy!
Woop, next step: my fit test samples arrived!
It's pretty fun feeling them just snap into place. Will test them with a longer wear later!
From their insta: faceplates are in progress!
@bleeptrack oh hell yes! this mouse's planets board is still kicking around, love this recycling step