What I like to do at home is this:
- Rip all CD's in as .wav using iTunes. I know, miserable. But it works. Also, you can rip them to an external hard drive for all the space in the world.
- Use an Airport Express near my stereo, then run my computer through Airport to stream to the stereo. Play through the apple remote using airplay.
This way you get convenience of thumbing through your entire library on your phone/tablet, create playlists, or even use it at a party using iTunes DJ at a party so guests can log on and pick songs like a jukebox.
I love my Sennheiser HD 280s (OTE) and they're only ~$120. Those are my beat around headphones. At the office, I use HD 600's (OTE) and could wear them all day. LOVE LOVE them. Gotta also keep in mind that they're open-back as opposed to the 280s which are closed back. Not an issue if you're in a relatively quiet place. I use the 280s on the airplane all the time and they work/sound better than any Bose "QC" bullshit in my opinion.