Headphones, earbuds, and IEMs have very different presentations. IMO, none match that of a great two channel or multi channel audio system. IEMs give you excellent detail and coherency and have the ability to control more factors in reproduction than do headphones which have reflection inside the earcup to deal with. Headphones do present better in a spatial sense in some ways. Earbuds are sort of a mix of the two.

I would definitely not say that headphones are superior, they’re moreso different. Also, they mess up your hair and put weight on your head the whole time.

The markup of most products probably would surprise you.

Hifiman has probably had the worst I’ve tried in their price range, but I haven’t really been impressed with most headphones cables under $400 whereas IEMs don’t have this issue even at $100 in many cases.

Companies seem to cheap out on the cable and it’s wild because they cost so little to have made in China.

Sony has a pair of wireless planar headphones on pre order today for $150 that also do lossless, I believe. So… there are options for planars at that price I’d consider over them.

These days, it’s completely different than in the past because there are so many great products available at low prices.

Some people would be satisfied by a Buchardt or Kef all in one system and the convenience would be a major selling point.

For myself, I like so many designs so it depends on the day. I could be happy with a nice pair of Genelecs or the Philharmonic towers with Purifi woofers, I also love my GR Research speakers and consider them to have amazing sound quality, but I do use subwoofers in that setup.

As you can see, very little would go toward electronics as there really isn’t value there, there’s moreso different tuning. I would grab a power amplifier (if needed) that has great measurements so a Purifi, NCORE, etc. A $100 DAC is honestly good enough (not worth giving up speaker quality). For streaming, a WIIM is “good enough.”