Well, if we're going with that theory - then shouldn't we all have bought Stax's when we first got into headphones? Hey, how come none of us don't have blockheads and such? Ahh....the $$ thing....
Plus, along with starting on the lower-end (which seems more practical to me), I've found that by slowly advancing your way up you develope a more sense of appreciation for your equipment as you can compare it to the previous models you had. Lower end stuff.
I don't know.....maybe just me then.
You go spend whatever you like. 
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Audio Setup:
Former Headphones : Philips SBC HP910, Sennheiser HD 545, Koss KSC 50
Current Headphones: Sennheiser HD600, PX100
Former Amps: JMT CHA 47
Current Amp: MG Head OTL w/ NOS tubes (GE 5751, Sovtek EL84s)
Former Sources: 2G 20GB iPod, Panasonic SL-CT570 PDCP
Current Sources: Audigy 2, 3G 10GB iPod, Sherwood CD-980 CDP
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