BUY USED!
...has become my mantra. Then you don't have to worry so much about "easing in" and losing a bunch of cash in the process. If you go ahead and buy a piece of equipment used, and take extremely good care of it, you can then sell it at or near the price you purchased it for. I like to knock a little bit off the price I paid because it makes gear sell quicker. I see it as an auditioning fee.
When I first got here in May I needed recommendations for headphones + mic to listen to music and play games with, and I did NOT want to buy an amp. I ended up buying some Plantronics DSP-500's and thought they were tha bomb. I remember back then seeing all the hype about the Headfive, and I was thinking, "$250 for an
entry level amp?! These people must be crazy or rich or both, I'm outta here!" So then I stayed away for a few months.
I came back I think in August, because I wanted to get some cans that would sound kewl out of my iPod, and I did NOT want to buy an amp. Then I made most influential decision of my short Head-Fi career: SR60's. omg. The Gateway Can. Suddenly, for some reason, some odd twist of logic, $250 for an amp suddenly didn't sound so bad. And look at the great deals on these k701's at northern sound and light, I mean, $240, these things go for like twice that much. Might as well get them. One month later: whats that? corda amps on sale? email jan? okies. What is a DAC anyway? Oh, really? Better buy one. This one looks good.
And the saga continues! Stello DA100 + Corda MKII-SE! And from Grado SR60's, I find that I am a Senn guy. The journey has been expensive, but TONS of fun. Very helpful community around here as well, I've PM'd and pestered several members who have been very cool and helpful in their responses.
Come, learn, enjoy. Just don't forget its about the music.