Well said. It's the perceived hypocrisy in hipsterdom that is seemingly so eyeroll-worthy, but to roll one's eyes, one needs to pointedly ignore the fact that we're all hypocrites about something.
I blame this on the deification of schadenfreude in popular culture. The advent of reality TV, and the prurient interest in other people's pain exemplified by the afternoon talk shows that predated it, gives us all not only the opportunity, but the permission and encouragement to feel like we're superior to others because of some dehumanizing glimpse into an uncontextualized portion of their private lives.
What a different world we might have if society cultivated a sense of humility, a 'hey, none of us are perfect and we're all out here struggling and I wish us all the best' mentality.
But then, fostering divisions and appealing to our baser, more ignoble instincts is more beneficial, both in terms of profit and also 'divide and conquer' social control.