I haven't read all of what was posted here.
I just cured my upgraditis by giving the final blow to my wallet. I have bought the headphone of my dream; even though it's not a company's flagship, it's one of their most appreciated headphones around here, definitely audiophile quality, a bit rare and on the costly side of things... okay I'm talking about a Grado HP2. I'm always thrilled inside when I think that I'm currently listening to the father of all other Grados.
But I didn't simply get on top of the chain on first blow, hence my upgraditis.. I went from SR325i, to RS1, to SR100-0, to HP2, and a few more in between for pointless testing purposes and, by lack of courage, not wanting to face my problem, scared by the thought of owning one of the top headphone in the world, thinking this wasn't for me.
I'm a university student and luckily I have received quite a lot of scholarships at my entrance for my good grades at the college, that the only reason why I have food to eat right now... or a HP2. If it wouldn't have been for those I would have never thought of even buying my first Grado (this September! yup), and without this first Grado it wouldn't even have been question of Head-Fi I did not know when I discovered Grado.
I suggest you that you start by finding a company you like. Find a shape of headphone, a sound, and make yourself a list of criteria, not just the sound, things that you want to find on the perfect headphone, make sure and plan everything so that you fall in love with the headphones of this company. Taking me as an example I wanted an open and full sized headphone (it could be a custom IEM, or a portable sized can, for more examples), that was of a round shape (it could be ergonomically shaped, angled driver, etc., split headband, just consider as much as you can when reading reviews) and that was not too hard to drive. I also dig the plain yet edgy look of the Grados and the raw materials used for their smaller cups. I think a good first step in finding a company you like is to go listen and touch to their lesser demoable choices at a Hi-Fi store or read reviews and impressions on Head-Fi about the company and their models, and most importantly the flagship / best offerings this company makes. I come from a small town where we don't have Hi-Fi stores or headphones from companies discussed on Head-Fi, so I have read reviews. You must already have an idea of the sound you want don't you? Me I wanted details, relative "musicality" (no matter what that means), and I wasn't asking for much bass at all.
Once you like a company, buy their flagship.
Lol. No I'm serious. Do that.
It could be just an AKG, K701, it could also be a Stax SR009. Those flagships are rarely deceiving to someone who just took his first step -- just think for a moment how happy you will be the day it'll enter your house, the day you'll open the textured rigid box with the nice leather smell or whatever headphone and box you have in mind --, but you have to buy only one headphone. And here's the hardest part to curing your upgraditis: content yourself of it. Don't try to change its sound because you don't like it (this issue should already have been ruled out way before you commit yourself to a purchase), don't become one of those merchanters to deal used headphones all day long, one headphone after the other, here on the classifieds section, and become overly nitpicky after having tried all the best in the world. Pick one up, and then start upgrading your system, very slowly... you are permitted to take your time because you have a world class headphone on your head and because it already blew your mind.
Later on you'll buy whatever other headphone you want or dream of another one, and you'll be able to sleep with two flagships instead of one if sleeping with headphones is what you want, yes. But right here right now what we want is to cure upgraditis! Let's keep our goal in focus.
So yeah in short, buy a end game headphone such as a HD800, a LCD3, a T1... whatever, a Fostex TH900. Save up all of your money for it, desire it for a while and plan it well because you know you will have to stick with it for a long time. Higher grade means better manufacturing means lower chances of failing means better durability means longer lifespan; -- even though some power-users at Head-Fi.org are actually rolling these things as random objects they own and don't care so much about to find a match with the latest state of the art headphone amplifier -- flagships are made to last you for more than a whole chapter in your life, which means many years. For me it is SO satisfying to have on your head a technological milestone (HD800), a wooden piece of planar magnetic art (LCD3), a magnetic field of a superior intensity of that of a MRI scanner (T1 or TH900), etc.
If you do just that I'm sure you won't end up owning so many random headphones, amplifiers, cables, mods, and trader feedbacks. I have purchased many Grado headphones for my part but now that I'm listening to a HP2 and I
definitely think I should have buy this one in the first place! But it was inconceivable for me to do so at the time. And that's what I mean when I say you need courage (kind of like this guy:
http://www.amazon.com/gp/cdp/member-reviews/A1JK8ZMM3WJWOK/ref=cm_pdp_rev_more?ie=UTF8&sort_by=MostRecentReview#R3OE19UCA8842F).
Right now I don't feel like owning anything more in life... okay, because I am BROKE, lol.
I am broke but I have found my guardian angel so everything will remain o.k. for me.
If you're too young, at school, or really just too busy to work for money or have money, then I'm sorry for you because you joined Head-Fi too early in your life. Buy something in between you and your dream headphone. A HD650 from Sennheiser, a RS1 from Grado, but not a model too low (
http://www.head-fi.org/t/596210/spent-so-much-money-and-still-disappointed) because you will end up spending even money. Chances are that if you are scared of your upgraditis to develop already then, it is that you already know about this phenomenon and what you will probably do after receiving your new headphone is visit Head-Fi always more and more to read reviews about the actual headphone (yes, about the one you just purchased!) and about the next step to take into improving its sound, or UPGRADEING it with another amp or something, and this is exactly what we want to avoid; the sad truth is that all Head-Fier wants to get the best out of their money, so they read and improve their gear. But yeah, some companies make great audiophile headphones at reasonable price. The FA-003 from Fischer Audio looks very neat. If you're not sure whether you can take care of something such as Sennheiser's flagship, then go for a smaller company and wait a little more before taking a sword and killing your wallet on a HD800.
Think about it, if you realize you made a fatal error by buying a Grado PS1000, which I don't even think possible, since this thing must sound incredible, you can ALWAYS resell it on eBay or Head-Fi. And reselling is easy to do, even though you loose a bit of money. Just take care of the thing while its in your possession and you'll be able to get back most of what you paid for it. Like I said, you should have read everything there was on the internet about a headphone (especially when its a flagship!) before purchasing it... I'm being silly with my "fatal error" thing but I just want you to remember that there is always and escape plan. Headphones are resellable goods and they have value... they are not garbage in = garbage out things, those are Skull Candies, headphones for the people who does not care about what their money can buy, who does not care one bit for their music they listen to only once in a blue moon, Skull Candy is the first headphone you offer to your child or I don't know, but these always end up in the wastebasket because no one cares about it once you have purchased it. When you've entered the top-tier, as long as they are repairable and that parts exists (which holds up true for most company and headphone, even my HP2 for which is still possible to have service from its maker, but not for the Sony R10 owner sadly), its virtually a timeless object that will retain 100% of its functionality... It's true that for cellphones, camera, computers, most of what's part of this huge and recent boom in the digital and computer domain of consuming, these things are condemned to become obsolete, but headphones do last a lot longer. Vintage headphones are still popular around and some of them still sound amazing even compared to nowadays offerings.
Next.
For the reason of the last paragraph, I think its always worth it buying used gear instead of new ones. I suggest you to do the same. You're doing a lot more good to the planet by getting someone rid of undesired goods instead of asking a manufacturer to create another one from the planet's limited resources. Also, even though some people here thinks their slightly used stuff is worth just as much as brand new in box one, which isn't true, you can snatch some great deals on Head-Fi, a lot more than on eBay, which usually ends up costing more because of all the visibility an auction get. Just know that if you want a clean headphone, make sure the seller doesn't smoke, have cats, or live in a tropical climate area... you can also ask the seller to clean his **** back to the way it was when he unboxed it. To mo, when it comes to flagship headphones, one needs to take utmost good care of it. "Babying" should be THE NORM when you've paid more for a silly headphone than you did for your car! In my case I have a 100% lettering HP2. That paint is worth about 500$ easily, and is super easy to rub off. I'm close to using cotton glove to manipulate it.
Finally, as another half step before taking up a grandiosity-level headphone and if you want to put upgraditis on pause with the use of the emergency button, buy one of those "proven-good" headphones They are headphones widely considered as safe bets and classics: Creative Aurvana Live! (or the Denon AH-D1001 equivalent or Fostex Kotori 201), Koss PortaPro, Fostex T50RP (you will want to crack this one up to modify it, I warm you), blox M2C (depending on your criteria's, some doesn't like full sizes), V-Moda M80.. just to name examples I know of, but there are a lot more of those, you just need to read and find out about them. I think the market is currently in effervescence for higher quality headphones, just go to site innerfidelity.com to discover a some thing very satisfying, and budget at the same time, just before getting your dream headphone.
Also, random idea and tips, conveyed as personal experience examples:
I don't like headphone amplifier or DACs, I think the law of the diminishing returns applies to them even more (
http://www.head-fi.org/t/472214/are-most-headamps-overpriced-cmoys). Those are of a realm even more niche where it truly becomes audiophile's play, and it gets very complicated if you want to attain a very specific sound with a specific headphone. I suggest you to stay away from it until you have found an headphone you truly love for just what it is, by itself (with no need to cover up for its flaws! in a perfect world all headphones should be like that). I still think the headphone is the most important part of the audio playback chain, because it has the most dramatic effect on the sound (obviously? it's the sole interface with your audition!). Me I've bought an okay Amp-DAC combo second hand, here on Head-Fi, for 300, and to stop thinking about it already. I think that as long as you have an headphone amp you're good to go and call yourself an Hi-Fier and invite your friends to come to your room and be impressed by your audiophile rig. Some headphones also sounds good unamped, that's very true for my Grados. I wouldn't recommend to skip the headphone amp part altogether to anyone, but for you, it will certainly help accelerate your curing of your upgraditis, to focusing on the headphone part. Buy one of these Chinese 200 to 350 dollars solid state DAC-Amp, Chineses know how to really give you the most out of your dollar (Dr Dac 2 DX, Matrix I mini, there are tons of them but I don't recall their names as they are all so similar and confusing, like the FiiO's E line).
Also I suggest that you forget about cables for now, that's jewelry for when you'll be older.
Portable amp is to be considered if you're buying a hard to drive headphone.
Remember to get wise and read a lot before buying any serious gear. You make less mistakes when you're wise, which might look obvious, yet we all eventually have to learn it the hard way, one day or another, and we sometimes repeat these mistakes in time... only human.