Normally, each transaction will cost you something.
The next question becomes - are you willing to go for "collector prices" or current model top of the line prices. Obviously, stick to the F.S. page for your first one or two ventures.
if you're new to "the game," i would take it step by step -- the pursuit is half the fun.
read head-fi, go to meets, browse in hi-fi shops and learn whats out there. there's much more than you can ever imagine and most is pretty good in its own way.
according to Buddhism that is the way life should be
but seriously... i went from well.. no over the head to HD595
then HD650
then well.. W5000
IEM wise, I went from normal ear bud>sony over the ear>E3C>E4C
each upgrade has somewhere around 200 dollar difference in their value.
but my next two upgrades would be a big step
one of them been getting either Stello D100 or Benchmade DAC1
the other one been getting well... the UE-11 pro (i figure by the time I get enough money for it, I am old enough that my canal don't change ... currently a 19 years old college student.)
Lots of small steps, side-steps, and steps backwards! Obviously, I haven't gone in with a plan, LOL.
Yes, the pursuit is half the fun. I'm currently on headphone hiatus (yeah, right), and I plan (hope) to carefully weigh future upgrades so I can step up in class with something appropriate.
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Phones (in order of purchase):
Sony MDR71, Sony MDR51, Etymotic ER6, Panasonic RP-HJ50 (the only major duds here), Shure E3C, Koss PortaPro 2, Creative EP630, Etymotic ER6i, Sennheiser PX-100, Sennheiser HD555, Future Sonics Atrio M5
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