Very interesting story!
I live through the same history...
But in reverse.....
I begin with speakers in a dedicated acoustic room...
All my headphones were not at all on par....
I lost my room /speakers...
I discovered after 6 months of optimization works on it the perfect headphone for me...
The AKG K340....
My system is so astounding now , the last time i triued to upgrade it, one week ago, i returned the headphone amplifier after one hour of listening...It is supposedly one of the best in the world ...😊 My sansui alpha certainly was one of the best in the world too...
Total cost of my system : 700 bucks for amp+dac+K340
Beat me in S.Q. and price !
😉
I disliked all 9 other headphones i tried, dynamic, planar or electro-static...
The only one who win on all acoustic counts is this prehistorical hybrid, the only hybrid success in headphone history... The K340...
I dont need anything else...
I cannot upgrade anything anyway.... It will be marginal improvement at big price...
Nobody here will believe me ... 😊
«Someone asked God why the ticket to heaven cost so much ?
If it was cheap nobody will believe it is for Heaven’s sake...» Anonymus book of jokes
I think there are two ways to look a at this. 1) from the fundamental differences from headphones vs a stereo audio system, and 2) quality of the sound.
While I have used pretty high end headphones for most of fifty years, I got serious in pursuing a high end headphone system about twenty years and now own a very good one (see my virtual systems).
i would have agreed that the two are just profoundly different until the last few years when I got really serious about getting my headphone system to be the best it could be. When I achieved this two things happened. Most of the instantly obvious differences between headphones and my two channel system went to the background. The headphone system became so involving the differences just ceased being that important. The second thing was that my main system sounded dry, steril and analytical.
So, my quest for a great headphone system begat a quest to get my main system to sound as good as headphone system. An additional $70K and two years later, I succeeded. Both systems (which is what I was going for) sound the same… minus the differences in the innate differences in the media… but it is not that big a deal.. I get sucked into listening to the music… not the system.
Ok, so back to your question. The theoretical answer I think is yes. Doing that by purchasing a set of headphones… no. It requires the same commitment and effort in assembling a headphone system… in today’s components: streamer, DAC, headphone amp and headphones that building a great main system takes. The good news is you can do it for roughly 10% the cost of a main system.