Simply put I prefer the intimacy that headphones provide. Unfortunately I do not own a high-end speaker setup of any kind. On the other hand I have listened to a several speaker systems that my uncle, cousins and friends own. Most of their stuff are in the range of $30,000 to $150,000. I've got an uncle who's spent more than $300,000 on his setup. They produce absolutely amazing stuff. I love the Cary Audio electronics that most of them have. HOWEVER, I'm a student, paying my way through school with what little freelance work I have. I spend a fair amount of time outside home, sometimes even staying over in school. So practicality points me towards a head-fi setup. Of course its a bonus that I love the intimate feel that a head-fi setup provides. I don't see myself getting a full on hardcore speaker setup till I start working or till one of my uncles feels generous enough to donate one of their uber high end setups = )