This is it? How can I upgrade the system?
(The following is a rambling of thoughts on your above.)
Ramble on.
It's a bit of a study in your own personal psychology. How do you listen to your music? How fat is your wallet?
As to gear? My take on it. First you start out with kr@p, you know it and you want to get as far away from kr@p as you can. Then you get the bug and you start drooling over the "expensive" stuff you really can't afford and then it hits you; how do you "really" listen to your music? And that becomes the mark you want to shoot for; esoteric vs reality. The whole thing centers on being able to hit the middle ground. Far enough away from kr@p so you won't feel like you've short changed yourself and centered enough so you don't feel like you've thrown a boatload of cash away on something you won't feel good about using, months down the road.
I came from a room system of speakers, transports, tubes and AVR's. Decided I wanted cool computer sound and found myself wanting more then what the computer had to offer; more stage, more air, more resonance, more dynamic range, more clarity and all of this at low volume as I don't like blasting my ears. I bought used or refurbished as that extended my dollar. Bought a couple of custom headphone cables and enjoyed the addition they brought to the table. Now? Now I have to be happy. If you won't allow yourself to be happy, then the process becomes a never ending story in the elusive of what doesn't exist; the perfect sound.
Soooooooooo, in a sense of the word, yes, I'm happy with the clean, clear, liquid sound I have. Even happier when I lightly EQ the sound to help pick-up shortfalls in the graphic equalizer's graph. Could I have better sound? I'm sure the answer to the question would be an unequivocal yes, but, at what cost and would I be happy spending that kind of money for such a limited amount of improvement?
But then maybe not.
That's called "audio-nervosa" and it's cured by not reading about stereo gear. As long as you keep reading about it, you're going keep wanting it and the more you keep wanting it, the more you're going spend and I'm sure it never stops until you decide to be happy with what you got.
Today, I made the decision to not buy another portable DAC/Amp that I can easily afford. Why? What, so I can leave it on the shelf, unused, but safe in the knowledge that it's there? Instead, I asked myself how do I listen to portable music and decided then and there I wouldn't use the DAC/Amp combo as cool as they look and I'd be happy with just the transport. So instead, I bought a set of referb'ed IEM's at half price that I had been wanting. But now, no more IEM's as after getting these, there's no point other than to spend, just to be spending.
A thought, a decent transport, a decent DAC, a decent Amp, a decent set of headphones with yes, a decent set of custom headphone cables and inter-connects above stock. Now? Now you get to define for you, what you consider to be decent. Usually budget is the deciding factor and remember, buying used is your fiscal friend. To sum up the above rambling, it's all about being happy with what you got as opposed to the grass being greener on the other side of the audio fence. Hope the above rambling helps.
Ramble off.

Edited by beeman458 - 10/5/10 at 9:14pm