Several points which don't flow well into paragraphs: 1) On-board sound isn't very good, in my experience. Admittedly, my 2006 Macbook sounds considerably be

Several points which don't flow well into paragraphs: 1) On-board sound isn't very good, in my experience. Admittedly, my 2006 Macbook sounds considerably better than my 2010 Toshiba. 2) My favorite headphones are the Etymotic ER-4P. I found mine online for a bit under $200. They're an almost perfect aural match for my beloved NHT 2.5i speakers. 3) The Boostaroo is a horrible amp. Unbelievable hiss and distortion. I don't know how they're still in business. If you need a portable amp, look for a CMOY in an Altoids tin, off eBay. Cheap and (IMO) vastly superior. 4) A computer's case is about the worst environment I can think of for audio electronics. Get any sound card which gives a digital out, and feed that into any consumer-grade receiver that supports digital decoding, like a Pioneer from Costco. This way, your uncorrupted digital stream gets converted to analog well away from the noisy PC case. You'll be 90% of the way to a ultra-high dollar sound for a couple hundred bucks.