For me it’s speakers then IEMs then headphones maybe 
The Chi-fi market rn is just way too competitive for headphones to keep up. Olina for $100? New Moondrop for $20? And the new RAPTGO plannar plus more to come?
I’d go end-game on speakers but I don’t got $10K (at least) to spare right now 
I have no uptime on headphones to justify getting them. And if I have, I would prefer to listen to speakers.
Im talking out of my a** here, as I have no clue whats the bare minimum for a good pair of speakers + sub + amps to sound great without overly paying for dimishing returns
I totally feel you.
I had several attempts within low-mid price headphone market and while I like the sound’s openess and note weight in general I naturally gravitate back to IEMs sooner than expected. It is partially due to the fact that I miss the convenience of usage - being easy to drive, portability and possibility of removal from one ear to hear someone out, but also the extra details I hear usually.
The second thing is I have heavy “hot-ear” syndrome, and normally after 1h of usage of even the most open, comfortable headphones give me this terrible uncomfortable high temperature feeling on my outer ear.
How is your Elegia btw?
Yeah I started with headphones, then found a world of IEMs, where price: performance is much higher than headphones IMHO. I have the Sundara, and I like them but my usage is max 5% of my total listening time. Quite heavy and my ears get hot
However for desktop usage I have powered close-field monitors for barely 100$ and details, convenience of usage, rumble and general SQ is amazing in my opinion, I don’t know how it does scale up from that.
Passive floor columns with dedicated power amp, sub and DAC is yet another story use case wide and money wise
Been happy with my around 100 usd 2.1 speakers for almost a decade now.
(Swan M10)
Have you tried earbuds?
The speaker route is like iems. The teas or the dusk depending on personal taste. There are better for more money but not everything more expensive is better. It fun but it will be somewhat more expensive. I would start with good pair of stand mounts and solid amplification. I just thought I say that. You know I am going to spend more than 300 sigh right now Lava and Dark Magician are interesting. Variations also but not sure on lower mids. I am sure your swamped work wise. Promotions mean more coin but more time working. That work life balance thing.
The difference with speakers is that you beyond the speakers, you need to have a good room for it. Otherwise you will be wasting money on the speakers…
Yea, I am one of your victims (LBBS, Qian39 in daily rotation and few more in drawer) and active preacher of earbud cult, but with no luck towards the anatomy as fit (or lack of it) is killing me most of the times. I even wrote couple of posts on this topic in your thread, but cult guru did not notice 
hahah, ops sorry.
Have you tried some other shells like the NiceHCK EB2S, Yincrow RW-2000?
It is shocking how much value you can get in speakers. When we moved, I gave mine to my son, since we were going to a smaller apartment. This move is really what pushed me mostly to IEMs.
The other nice thing is that for people who like to tinker, speakers are perfect. There is room to work, you can replace drivers, crossovers, wiring, and enclosures. If you really want to get nuts, you can even make your own crossovers, and try different wiring.
True though for many designing and building g crossover might be better left unattended
the 3.1 diy kit was great still using them as my living room speakers
think I had some $100 edifier speakers that were great for the money but gave them to family when I got some Klipsch’s on sale
hoping to get the Micca RB42’s next time they have a flash sale (usually sold out before I notice rip)
Good luck I realize these are possibly a bit more expensive but Paradigm was a good value for money. I been out of it for awhile though I kept my totem hawks. You can ideally do well buying used btw as audiophiles are very truthful about the condition and have always been very honest.
Sold 2 days after I got a cable for it. Hot ears, meh sounds compared to my IEMs, EQ, etc.
Yeah, guess what I’m interested on? 
Actually both, but the end game is floor columns.
Was about to say this lol
That’s the main reason I need to move before I can even think of it. that a few raises lol
Lower mids are a problem, on Variations, with my library.
For my preferences:
DM > KL >> Variations.
I do prefer KL over regular EJ07m, but they are close. It’s really a matter of personal preferences at this point.
Horrible, but have been holding up since all my packages are delayed, I didn’t have to get any free time to review stuff. Will receive a lot of stuff this week tho.
Yincrow is way to expensive for my taste at this stage of addiction, EB2S or one in similar shell I would maybe try if my next fit-workaround (silicone hooks from shopee) won’t work
Last resort would be those earpod-like shells. Like the Yincrow RW-100.
That or otoplasty
Those work for me.
The EB2S shells work for me for the most part. The typical Bud shell (@Rikudou_Goku what’s the name again?) hurt my right ear after about 30 minutes.