I have found that using the equalizer in Foobar2000 has a HUGE impact on the perceived sound quality of my headphones. My Sennheiser HD280 equalizer settings completely transform that headphone, in my opinion, from something that sounds pretty awful (compared to speakers) into something that sounds quite enjoyable. I've also been able to improve the sound of my Qualia headphones (with a slightly greater emphasis on midrange) with an equalizer.
In my opinion you will derive much greater benefit from good equalization with headphones (and speakers) than by endless experimentation with components and cables that might bring you slightly better bass, midrange, or high frequencies when used in the right combination. Of course, once you've achieved all you can with equalization, you'll need to start upgrading your hardware again. But start with the software (or relatively inexpensive equalizer hardware), it has far greater bang for the buck.
