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I would say that noise from surroundings makes huge impact to sound.
So counting for the same amount of money, headphones will always win.
I had a hard time transitioning from headphones to speakers because of this factor, and the lack of coherence displayed in many multi-way speakers (versus a point-source driver). Then there's the higher expense, and the overwhelming pool of choices that can't be easily swapped in/out like with headphones. It's a lot more difficult; hell it's quite easy to assemble an expensive speaker system that sounds awful.
You can't run serious speakers in a bad room (e.g. small bedroom, low ceiling, crappy construction quality) and not experience seriously negative room interactions. However, with good speakers and a decent room, the latter becomes more of an asset than a liability. I like running a close to near-field setup (e.g. 7-8 feet away from each speaker), which significantly reduces the severity of room interactions. Further out is too far IMO. My speakers are also a phase-coherent point-source coaxial, so they're just as coherent when close-up. They also have a horn-loaded compression driver (handling from 1K up) which further reduces the effect of room interactions without reducing the sweet spot to a pinpoint (you want it just big enough for you and a couple of lady friends
). I don't want wide dispersion, and I don't want beaming -- controlled dispersion is best. Also, furnish the room sensibly! With some furnishings in play, a little bit of acoustic treatment goes a long way; you don't need to spend a lot of money piling them in there. Don't have your gear and chair as the only stuff in the room. If the room looks like a nice and comfortable living space, then chances are it won't sound terrible either -- though this doesn't give you license to botch the speaker placement with a WAF-approved location!
An additional point in the headphones vs. speakers debate: headphones may have some inherent advantages, but speakers have always had the far bigger market share (in the high-end). There's vastly more money and demand there, so there's been way more R&D spent developing speaker cabinets & drivers, and high-end speakers are more likely to benefit from high-tech materials and manufacturing techniques. The best speaker drivers are of better quality and far more impressive than the best headphone drivers.