I have much more experience with headphones, but sometimes an IEM would be more convenient. In an attempt to provide information that will be useful in generating recommendation(s) for me. I will mostly talk about my experience and preference with headphones. (I hope that is useful). Looking at around $100 and used is completely fine.
Genre: EDM primarily (Dubstep, chillstep, trap, progressive house, ambient, lofi)
Current Headphones: I have the HE4XX and the 6XX and much prefer the HE4XX due to the wider sound, and less forward midrange. Basically, a HE4XX in an IEM would be great.
Preferences: Spacious sound, quality bass, laid back rather than forward vocals is preferred. Timbre isn’t the biggest concern. Bass slam and some air from the treble are nice-to-haves.
Gear: Silicone Tips (small). Will be using straight from my macbook for a while but plan to use JDS Labs ODAC -> LCX when I am back at my apartment.
Earbuds would be great due to comfort, but from my understanding, the sound doesn’t compare and there aren’t really any good sounding options (other than maybe that one from Moondrop for like $250 iirc).
Let me know options would be a good fit for me and what highly regarded options don’t seem to fit my preferences so I can be sure to avoid. Feel free to chime in with options above my price range, so I can keep a future upgrade path in mind. Trying to learn more about IEMs