You using a splitter of sorts
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To sum up what I have heard so far:
Things people probably mostly agree on:
- Headphones/iems are convenient in lots of scenarios. Require very little effort.
- Speakers allow group enjoyment. Require significantly more effort.
Things no one agrees on:
- Absolute sound quality of speakers or headphones.
- Cost to value of sound quality for speakers or headphones.
Does that sum this up?
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As Douglas Adams thought us, the answer is usually easier than the question.
1). Better than what? Better value for the highest fidelity per dollar?
2) Better for when? As noted by others, with others sleeping, any option is a better option than nothing.
3) Better at what? Better at reproducing vintage Fugazi tapes? Better for listening to a collection of North American passenger trains?
The people at Roon have certainly found out lately that you never really know how people are using tools.
So. It may be a. better value for you, right now, with what you want to do. Or it might not. Maybe you quit looking at speakers before you got to the level of satisfaction IEM have given you. But that wouldn’t have to do with value, but accessibility for you.
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So you’ve been to some of the awful rooms at Axpona as well? 
I have put together a modest 2.1 for listening and a higher end soundbar plus sub for movies. The soundbar does reasonably well in a less than ideal room and kept down costs. This freed up more funds for headphones and the separate 2.1 system.
My next audio upgrade will be room treatments, especially the hanging ceiling tiles that vibrate with certain bass notes. I am thankful that I have been able to build a great headphone and 2.1 system over the years. Now that I have a home where I don’t have to worry about the neighbors, I look forward to building a bigger 2.1 system over time.
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I stopped listening to my very nice 2 channel setup when I got married, 20 years ago. Just for practical reasons.
If I had a custom-made listening room/man cave that prevented sound escaping elsewhere, I’d probably be listening to more 2 channel than headphones. But I have no regrets, I love my wife and my headphone system, so I really have nothing to complain about. 
I do have a very nice 5.1 home theater setup too, that we both use extensively, but it’s much better for TV and movies than music. I have huge Definitive Tech speakers with built in subs, that radiate a lot of the sound backwards or sideways. This adds a lot of atmosphere to movies, but the center speaker (which also has a built in sub) anchors everything. But using just the main speakers for music is a little too diffuse.
I’m a headphone guy, not a big fan of IEMs, which I only use for traveling or commuting. On the other hand, from reading reviews on this forum, it does appear to me that IEMs are better value for money than headphones (i.e. less compromise in the sound quality) in the $100-400 range. That’s just the impression I get from reading this forum. Moving to the other end of the price range, maybe I should have signed up for the Odin tour, to see how a first rate IEM compares to my Verite and Stellia.
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Does it really matter if it’s accessibility, money, boredom or stupidity that makes one better or not?
The point here is to talk about your likes and dislikes and why. Do you prefer one over the other? Why? Which do you use more? Which one fits your life better? How do you use it?
I always wonder what kind of lives people have with dedicated listening rooms. Are they retired? does their family use it too? I have a good sized house, and I don’t have nearly the space to dedicate to such an adventure. So, ditched the system when you got married? For me, it was kids that killed the home theater (technically kids and moving).
And never mind the space, even if I made the space available, where does the time come from? 2 young kids and no external activities during covid? Nope. There is no such thing as “listening session”. Have to listen while cleaning the kitchen, picking up the playroom or responding to random life stuff on my phone.
Wish I was able to get in on odin. I want to know how far this IEM thing could go.
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Acknowledging OPs subject line “value” is far more elusive than system types/setups.
Simply put (and a tried and true opinion) all in all it’s:
- Speakers
- Headphones
- IEMs
Are you saying that is the value order for you?
Sorry, didn’t get that. What do you mean?
Nope. SQ/the listening experience. I value my headphone setup far more.
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The 1.8 update busted a lot of use cases, people that cataloged live shows were really hosed by some choices that seemed obvious to people that listen to albums and stream.
Thank you! I am a recent roon user and still discovering it. I read some discussion around the update, but wasn’t aware of that. Will check it on other thread.
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Maybe not worth you time? Internet outrage is nauseating.
I had to mute several threads I had been following.
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Getting the music to the headphone amp and headphones can still be pricey if you want it to be… 
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Spot on 20 Characters
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Due to downsizing from a house to a condo, I went from a dedicated full-blown 100 inch home 7.1 home theater and totally separate 2 channel audio system (MBL speakers, Macintosh amps, EMM DAC/CD transport) which was a major investment for me, to:
a 65inch LED TV with Bose Sound Base, Woofer and rear speakers (works fine for movies) and Tidal/Qobuz streaming into a great DAC and amps and TOTL headphones.
Because my wife is extremely sensitive to sound, the new setup actually works better. She is very satisfied with the sound of the TV/Sound Base, and doesn’t share my addiction to Classical and Jazz music.
So, for a much smaller investment overall, I have balanced the availability of space, with the desires of my wife and myself. It is a happy compromise, and my ability to appreciate great music is not diminished at all. In fact, I would say that today I probably get more “ear-time” with the headphone system than with the previous 2 channel audio system.
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I understand the journey to personal audio, and perhaps the manner in which I view the options you listed in the first post:
Home Theater: Movies/TV and any video content/Music if I am watching a concert or something else encoded in multi-channel
2.1: Music
Headphones: Music
IEM: Music
For me they are all tools to be used in any given mood, need, etc. Which of these provide me the most joy, it is not necessarily dependent on the tool being used. Maybe I am a crazy one, in all four of the above I have spent the most money in the shortest period of time on my headphone set up. I think it is a road I was always hesitant to go down as I knew what would happen, I would dive deep into it and start investing money into the whole system.
Is any better than the other because I spent more money or bought better equipment? No, cost has nothing to do with it. I could probably be happy listening to the HD6xx through an OTL with a $600 DAC. Actually, I was very happy when I had that set up.
The irony is I have had a variety of headphones since I was a teenager listening to my Sony Walkman:
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What if you could only have one?