Don't listen to advice. Go listen to expensive headphones. And remember you'll need a good amp/DAC to pair with them. If you throw $1000 at LCD2C, throw $800 at a decent amp/DAC, like a Fiio K9.

Seriously though, you can learn a lot through reviews and frequency response graphs but you have to hear headphones. Go to Hifi and headphone shops. Talk to dealers and ask to audition stuff. Some will send you stuff to try. Some audiophile forums out there have reps from these companies that will loan you stuff to try. The best option by far though is a hifi shop that has 100 pairs of headphones out to try.

There are so manyh variables out there. Even saying "I really like bass/midrange and I enjoy hip hop" is not enough information. Even if you added more information its still not enough, because everyone hears differently. To use your own example- you know how you have that ONE friend that looks at your 144Hz monitor and says "I dont see a difference"? Audio is like that.

Go try headphones. Tis the only way