There are at least 3 different audio stores near where I live that have $20K+ speakers set up in quality demo rooms with proper acoustic treatments. I don't know of a single place I can go where I can try out headphones worth more than $500. Perhaps my experience is unusual, but I suspect it isn't, and that makes this question a tad difficult to answer.
Both speakers and cans seem to have logarithmic price/performance curves. (i.e. The difference in quality between a 10$ set of cans and a $100 set is far greater than the difference in quality between a $100 set and a $200 set.) It seems to me, just based on what is available, that cans tend to level off at a lower price than speakers do. That doesn't really have much bearing on cost-no-object setups however. I haven't heard the best speakers or cans out there, so I have to reserve judgment for now.
Surround systems tend to be maligned quite a bit by two-channel listeners. There are several valid reasons for this and corresponding workarounds:
- Most surround systems are used as theatre systems, so a big honking display of some sort is typically found in between the front speakers. This wreaks havoc on the left and right main speakers' imaging. Workaround: Use a projector instead of a television or plasma display. You get a bigger visual image for less money and less interference with audio imaging. The only downside is that light control is now an issue.
- Because of the dominance of the screen in a theater system, many people push their speakers off into acoustically unfavorable positions. (e.g. Into the corners of the room or right up against a wall.) Given a big enough room you can get the speakers into a more favourable position however. You can make surprisingly few compromises to two channel performance when setting up a theatre system if you take care in what you're doing. Most people don't however... It is an unfortunate truth that the most acoustically favorable positions for speakers is seldom the most convenient positions to live in and around.
- More channels means dividing your money amongst more speakers and amplification. To get the same quality in a multi-channel system you have to spend more than you would for a stereo system. There's no workaround here. No matter how much you spend on a multi-channel system, you'd be able to afford a better stereo system with the same amount of cash. However, if you're far enough down the price/performance curve differences may well be negligible.
- Multi-channel processing sounds awful. Yes, I agree. It's hideous. I have no idea how people can listen to stereo music in dolby pro-logic 2 or even Lexicon's mystical circle surround. I, like many others, let the source dictate the means of reproduction. Stereo music should be reproduced in stereo. 5-channel DVD-A or SACD on the other hand...
- Surround speakers are crap. Well, they are if they all came in the same box! Bose Lifestyle and B&O systems are bad enough, but then there's all the Home-Theatre-in-a-Box rigs at your local electronics store... Honestly though, how many quality sets of cans do you find in the same places? There is better stuff out there, so don't judge all surround setups by that crap. Furthurmore, practically no consumer electronics store is going to bother setting up speakers properly. Even high-end stores rarely have enough space to set up even one tenth of the speakers they sell properly. It is comparatively quite difficult to mess up the setup of a pair of cans. (i.e. Place cans on head. Plug them in. Press play. Done!)
Anyways, personally I have a set of ~$150 cans (Shure E3's) and a somewhat more expensive surround system. (Onix Rocket RSC200 + 4 x RS750's, Bryston 9BST, Anthem AVM20, Paradigm Servo-15) I bought the E3's for when I'm out of the house and they do an admirable job. There's absolutely no contest between them and my home system however. (not even when I'm out of the sweet spot!) Of course, I never expected there to be. I'd love to hear some of the nicer cans out there, but, as I stated above, it can be a tad difficult to audition them!