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Ya I think I'm starting to lean this way. The tough part is that certain cheaper headphones can do a lot of stuff better than the more expensive ones. If I made a list of 10 things that I wanted/needed out of a headphone, and one headphone did all of them well, that would seem like an easy choice. But what if two headphones could do 5 out of the 10 even better, but weren't as good at the other 5? Then potentially you could have two headphones that meet your 10 requirements better than the one.
Sorry if my question didn't make any sense haha.
I get what you're saying perfectly. That's part of the dilemma I've had with certain headphones; better at some things, worse at others.
For instance, the SR-202; it had much of the characteristic Lambda presentation, and I wouldn't be surprised if it was technically superior in some aspects to the vintage sets like transient response and frequency range extension, but the original SR-Lambda just had a superior midrange to my ears that an EQ bump couldn't replicate on the SR-202. There was also the matter of comfort; that Nova/numerical series headband/arc clamps significantly more, enough to make long-term use sessions (say, during heavy gaming) uncomfortable, even with nice, soft pads like on the SR-303 and higher-end models. As it turns out,
newer, more expensive models weren't always better, and for as much praise as the SR-Omega, SR-007 and SR-009 get, I still have my doubts that I'd take them over the SR-Lambda if I got the chance to audition them with my choice of material.
There's also the Panasonic HTF600, a headphone I thought was an okay cheap set at best until I got a Philips CitiScape Uptown later on at around twice the price. The Uptown actually didn't sound as good to me as the HTF600 did overall, mostly because of the crippled soundstage with no depth that makes them unsuitable as a gaming set, though the Uptown performs very admirably for music listening. However, it's now taken the role of my portable full-size headphone because one of the HTF600's drivers crapped out. Sound quality doesn't mean much without reliability, and you'll find that if you have to replace cheaper headphones too many times, you could have afforded something of better quality.
You'll find that choosing headphones isn't easy, especially when you're still trying to figure out what your sound presentation tastes are and considering all the factors that don't have to do with the sound, like comfort and reliability. But along the way, you might find some startling revelations, like how the headphones you've had all along may actually be your favorite, and you just didn't realize it until you listened to all the other popular headphones and didn't like them as much for any number of reasons.
I just think you're more likely to find your personal 10/10 headphone at the higher price ranges. At the very least, $400 is where you can consider second-hand electrostatics and orthodynamics, and I would definitely advise auditioning one of each at least once along your headphone journey. Don't like it? Return or sell it, then put the funds toward another headphone.
Oh, and definitely keep in mind what other people have said about the rest of your audio chain. I've read all those posts about $200-250 headphones requiring equally expensive amps to get the most out of them, or for them to function at all if you're talking electrostatics.