First - go to headfi.org to get the best feedback on this subject - its all they talk about and there are some very versed people on that site. There are also classifieds if you want to buy used.
Headphones are a great approach and one can far exceed the performance of an outloud system at a fraction of the cost/price. First thing you need to figure out is what type of sound you are looking for from the "cans". You may be best off hitting a store than sells a variety of brands and listening - at least getting an idea of which brands produce a sound that is most conducive to your tastes - then going to Headfi with that info for further suggestions.
What part of the country do you live? You should post that so others who have "phone" systems could allow you an audition of theirs - garnering you some experience for likes and dislikes and helping you get started in the right direction.
Headphones are a great approach and one can far exceed the performance of an outloud system at a fraction of the cost/price. First thing you need to figure out is what type of sound you are looking for from the "cans". You may be best off hitting a store than sells a variety of brands and listening - at least getting an idea of which brands produce a sound that is most conducive to your tastes - then going to Headfi with that info for further suggestions.
What part of the country do you live? You should post that so others who have "phone" systems could allow you an audition of theirs - garnering you some experience for likes and dislikes and helping you get started in the right direction.