I live in Montreal, a city with 4 major universities and a reputation for the particular things that hipsters find so attractive. As a result a significant population of 18-30 year-olds in my area are hipsters. I've been considered one, my roommate is definitely considered one. I only have problems with them insofar as I think their particular choices of style are absurdly stupid and because a certain population of them are extremely elitist. Personally I understand a lot of it: bikes are a really good way to get around in Montreal (even if I don't think fixies are the most practical thing ever, they are low maintenance), PBR in Montreal is very, very cheap so is an easy and flavorless way of getting drunk, and I don't really have any problems with the music hipsters listen to even if some of it I wouldn't listen to myself. I do think that ironic tattoos (tattoos being something I'm very passionate about), low-cut v-necks, skinny jeans, non-functional glasses and dirty mustaches + lesbian-style haircuts look dumb overall. Again, though, it's not hurting anyone if they want to look like idiots. Hell, I know a lot of hipsters and they can be really nice people. But, and it is a huge but (heh... huge butt), there is a small pocket of this group that will judge you for every bit of your person and those people I cannot tolerate. Here are two recent examples that I would say are the elitist population comprising a third or so of hipsterdom:
Story 1: Yesterday I was in the bookstore buying books for a class of mine (I only need books for one of my classes, since all my others are studio courses). I bike everywhere in the city because it's cheap and fast and I like the exercise. When I'm walking around, I have my helmet attached to the strap of my courier bag. As I was buying my books, the cashier looks at my helmet and my biking gloves and promptly poses the question "So what do you ride?" in a smug sort of way. This is a question I often get asked and what they want to know is the exact details of your fixie. I don't ride a fixie, I ride a very practical, functional and fast diamondback hybrid. I stated that I ride "a hybrid" since I had a class to get to and I was in a hurry. His response was a mocking "Oh..." as if I was some kind of idiot for riding a hybrid and not a fixie.
Story 2: This one happened to my sister a little while back. At a party she was being introduced to a friend of her friend who was visiting Toronto from out of town. The first thing he asks her is: "So what kind of music do you like?". I hate this question. It's the kind of question that, as an adult, you only ask if you're really interested in telling people about your own musical taste. My sister, trying to be friendly and accessible, instead of listing anything obscure begins listing more well-known artists that she enjoys: Tribe Called Quest, J5, Biggie etc. When my sister reached Biggie on that list the guy says in a skeptical voice "Oh yeah? You're into Biggie? Well go! Rap some Biggie!" Never before have I encountered someone who you had to prove your musical taste to. Someone who believes that he, in his infinite wisdom, needs to weed out people who don't actually like certain music by making them sing it. Now, my sister is a bit too nice of a person to actually give him shit for this, and she really easily could have given that she knows most of the album Born to Die by heart, so she did "prove she likes Biggie". Still, she left offended.
It's this kind of douchebaggery I can't stand. The kind of person who believes it is their right and their privilege to judge other people's tastes based on their own elite criteria. But the thing is, this isn't exclusive to hipsters at all. Every sub-culture is elitist. It's the reason I stopped enjoying being a punk, back when I was into street punk. Punks only like people who like punk. Everyone is shit to them. Take gamers, even. Have you ever judged someone for their taste in games? Or been judged for your taste in games. It's the same bullshit. Hipsters happen to be a really easy target because they look ridiculous and are incredibly widespread, but all subcultures are guilty of the same stupid shit.
Bottom line: I know very nice hipsters. I think hipster style is stupid but have no qualms with them in general. All subcultures tend towards elitism and they are all guilty of it, even if hipsters are the easiest target. If I encounter a hipster who is a douchebag it is on their own merits, not by the fact that they're a hipster.
EDIT: Also, can we put this whole "I did this before it was cool" thing to rest. Every asshole does that these days, not just hipsters.