I dont think most of you use the term hipster correctly (same with most media outlets). Ive seen articles calling people hipsters for "GASP!" growing vegetables in the city! Or riding a bike! Or listening to music YOU DO NOT KNOW OR DO NOT LIKE!
But what is a hipster? I dont think "hipsters" would care about Vampire Weekend or Pretty Lights or the Avett Brothers.
Isnt a hipster someone who THINKS they are cooler than everyone else based upon their musical taste and other criteria (clothes they wear, movies they dig, books they read)? IE UNDERGROUND?
Maybe it is because I am towards the younger end of the spectrum on this board, that i do not throw out the term for everything and everybody that is different.
Further reading:
http://en.wikipedia.org/wiki/Hipster_%28contemporary_subculture%29
I think for some of us, the term hipster has positive and negative connotations. For example, there's the "Portlandia" context that you describe (bike-riding, growing veg, composting, etc.), which I think is positive. It's easy subject for satire though. Then there's the negative context, which is more about people thinking that they're superior or maybe cooler for liking stuff for the sake of being different, not because it's good or better. I think it's what happens in one's 20's when you struggle for identity. In the 60's there were hippies, in the 90's there were ravers (just for example). I don't think all young people are hipsters, and not all hipsters are bad. But if you were to go to Brooklyn, Austin, Portland (heck, even parts of LA), etc. you're going to see that hipster isn't exactly underground. In fact, it's probably the norm.