Thanks for all the helpful suggestions! Unfortunately altogether they contribute only to my bemusement..
I suppose I could elucidate on my sound preferences right now. I listen predominantly to trance, techno, and electronica. Other genres I frequently enjoy include post-grunge, metal, rock, trip-hop, and a sprinkle of classical. The former set contributes to approximately two thirds of my listening, while the latter set accomodates a third of its own. I appreciate a forwardness and definition but have grown to dislike flabby bottom end. What I ideally enjoy is a full but tight bottom end with appreciable mids and treble that are far from recessed. I like presence, definition, and resolution; I dislike flabbiness, recession, and overwhelming sibilance. This may sound blasphemous but I am not used to soundstage. I don't know whether I like it or hate it, but in general my listening has never contained rich soundstage or such perception, and I am patently unsure about the prospect, though I am sure it would be interesting.
The prospect of a flash player also seems alluring. I've been contemplating a flash player for recreational purposes when the size of the X5 becomes unwieldy. I'll look into the Philips; there seems to be a dearth of appealing flash players under $100.
The Sennheiser HD555.. I'm interested, but at the same time I'm chary. I'm not extensively familiar with the sound signature of the bigger Sennheisers, as I've accustomed myself mostly to some of their sub-$50 offerings. I'm mainly curious as to how they'd perform with my preferred genres and whether they'd hold semblance to my preferred sound signature.
The PA2V2 and Go-Vibe seem like excellent amp options that I might look into. My interest in amps is rather wishy-washy but continues to grow slowly. I've read comments that alleged that amps only contributed to some 10% of the final sound signature, and yet many praise them without reservations. I also use my Cowon iAudio X5 for most of my listening, and since the line-out of this device is seriously hampered, I'm curious as to the true impact of an amplifier when fed the headphone-out signal. I was also curious on how either of these amplifiers might effect the sound signature of my independent headphones (again, iM716, ER4P, KSC75). My readings lead me to understand that the amplifiers will contribute much to the airiness and soundstage of the headphone.
The Grado SR-60 also seems very appealing to me. I've always been interested in them because of the probability of my liking it (since I'm rather fond of the ER4P). However, I've been hesitant as I'm unsure these would see much use. I do very little at-home listening, but I was wondering if the SR-60 was good enough to change that. My listening environment is usually rather noisy. Also, I've read about them frequently and had an equally large concern: would they be too similar to my KSC-75? I'd be somewhat distraught if one supplanted the other as it would hurt some of the variety I enjoy with my meager set.
Thanks again for the suggestions, I'll do some more contemplative musing.