I like headphones, though, because you can still get 99% of the original sound at a fraction of the cost of a huge multiple-speaker system. It's hard to simulate the scale and stage of large speakers, but most people are willing to sacrifice this for convenience.
Not me.
I still opt for vinyl over digital. Now I will admit that these days, digital is so good that it **can** sound as good as vinyl. But back when I put my system together, redbook cd's were no match at all for vinyl. But I have over 1,000 good vinyl recordings, so I'm not looking to make the switch.
But headphones have never worked for me. What I hate the most is that there is no way to get spatial realism from headphones. On my main system, I worked hard to make sure all the instruments are represented in much the same way they are in a live performance (well, assuming it was recorded well). It really is fun to listen to music on a good system, but I really get very little joy listening to music on a system that just lumps everything together (and even misses a lot of what should be in the recording).
Audio is a pretty strange hobby to still pursue in this day and age. 20-30 years ago, having a "kick ass system" and some "b!tchin' speakers" was a big deal. Now its all about how small and convenient it all can be. How many thousands of songs you can pack on to a device the size of a matchbox.
EDIT: I see you also referenced multi-speaker systems. I'm a dyed in the wool two-channel guy. Surround sound might be OK for movies, but it is awful for music IMO. It really distorts the spatial realism that I prize so much. I do have acoustic panel in my listening area so the sound is right, much like a music hall has to work hard to get the sound right. But I'll never go to surround sound / multi channel for music.
.......ahhhh, nothing better than listening to a Haydn or Mozart symphony on vinyl through a low watt tube amp powering a nice modded pair of klipschhorns. It's like the orchestra is right in your room. I never get fatigued. I could listen all night. Listening to the same thing on my ipod is like listening to another piece of music entirely.