Sure you can run an extender, although that will both increase the price of your phones and tend to downgrade the sound slightly, owing to the extra cable and especially the connectors.
As for phones to try out the concept with, sound quality and comfort are the priorities most people mention and the less costly Grados score high for the money in the first category. Some people don't like the way they fit though.
I'm not a great headphone user, but I need them for some things. I have a pair of Grado SR60s and also a pair of Sennheiser 580s. The Sennys are far more comfortable, and better-sounding, but they cost a lot more.
As for phones to try out the concept with, sound quality and comfort are the priorities most people mention and the less costly Grados score high for the money in the first category. Some people don't like the way they fit though.
I'm not a great headphone user, but I need them for some things. I have a pair of Grado SR60s and also a pair of Sennheiser 580s. The Sennys are far more comfortable, and better-sounding, but they cost a lot more.