About 6 years ago, in a span of 2 years, I went from a Sennheiser HD201 + ipod to the Sennheiser HE90 + Singlepower ES-1, with about 50 stops in-between. Today, I have a pair of Usher monitors that I bought for $1000 locally (and a Linkwitz Orion that costs about $2500 to build). For me, the jump in my enjoyment was greater when I went from the HE90 to the Usher (I'm not even going to mention the Orion, which is just in a different realm altogether) than when I went from the HD201 to the HE90. I guess that makes me a speaker guy, eh? Still enjoy listening to headphones once in a while.