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wouldnt it be worth putting the money towards a new set of cans/speakers? atleast to me the biggest difference is made at the driver end of the chain as long as the stuff in between is decent
In many ways setting aside a large portion of your system budget (should you have one) towards the transducers is the wisest thing you could do. The hard part is finding out what you like and what headphone delivers your ideal. Once you have settled on a headphone that meets or exceeds your goal then you can concentrate on the other pieces paying close attention to what works well with your transducer choice. I would say the choice of the headphone is slightly less important than source quality although both parts of that system equation can have dramatic effects if either is not up to snuff (able to extract the max performance from each other). Having complimentary parts of the system is the key to having a great experience or end result where potential of the individual pieces is realized rather than hindered by the combination as a whole. Easier said than done which is why Headfi is a good place to find a lot of great tips and info towards making as few purchase mistakes as possible when starting from scratch (or one is a beginner in the audio hobby).
Here is how I would judge a basic system's priorities when starting from scratch.....
no 1 - source quality is crucial as everything after this stage will be effected ( adversely or not ) downstream from it. Major issues with your source cannot be corrected by the amp or the transducers only masked to a small degree.
no 1b - the quality of the transducers is right behind source since none of the systems capabilities will be realized in full with sub par cans/speakers what have you
no 2 - amp quality, voicing, synergy with source and transducer and how well it deals with the source signal (drives the transducer load) in terms of transparency, fidelity etc is part and parcel in a good "system". There are few really bad amps I've found out over the years, most of them do a fair job. Again a great amp fed by a great source will get one step closer to the max potential of your chosen speakers/headphones.
no 3 - ancillary components like cabling (mains cables, IC cables, digital cables) can have positive or negative effects, again it depends on what works best with your system and the headphones chosen. Some say finding the right cables for your system that also match your budget is one of the harder parts of a system build to get right. Due to the contentious nature of cables being important (cheap vs expensive) in an overall system's percieved max result is an argument that will never end. I'm a cable guy for the record FWIW. Experimenting here is something you should consider once you have the base pieces of your system solidified and well matched. Changes can be anyhwere from subtle to quite palin (good and bad).
no 4 - giving your system a decent clean power source and a decent rack to sit on is another important factor if you want get the most from your gear. Again this part of the audio world has many supporters and I'm sure just as many detractors. I think having decent clean power and a solid rack for the gear is always better ...some folks can't hear any improvements...this another YMMV and it is last on the list for a reason.
Really 1 and 1b are the bedrock of great system IMO.....
Hope that helped a little,
Peete.