You say hipster, I say interesting :P
If those are the qualifications of being a hipster, I guess I'm somewhat guilty too! I have definitely been (jokingly) accused of the same heh.
I definitely get the sentiment when it comes to the shoddier/flawed quality of records and such, I have the mentality when it comes to games too, there's a certain charm in the older, grittier style at times, and modern games can be too polished and refined almost to the point of feeling soulless. Though when it comes to music I tend to go for the best quality because to me much of my enjoyment of music stems from - or is at least enhanced by - the depth, crispness, and overall quality which helps immerse me into it. Stuff like films really just depends on the overall story, writing, settings, etc. Love the super glitzy stuff but I can also enjoy, say, 12 Angry Men or Wizard of Oz.
I'm sure your last statement is meant to be tongue-in-cheek but still, I'd answer that with there's nothing to "remedy" and to not give a crap what image you convey. Whatever makes you happy is what you should roll with!
"We hold these truths t-be self-ful evident. All men and women created by the.. Go-you know the.. you know the thing!" - Joe Biden