Lemme get this straight. A discrete soundcard or external dac is usually recommended (over integrated audio) for listening music on the desktop, but a smartphone(post #3) or a sansa happens to be alright for a good headphones?
OK, I have no idea where you are coming from and it would appear that most of the rest of us don't know, either.
Only your ears know the difference.
So, I think it is appropriate to calibrate my own listening ideology so you can relate to my tastes or discard my recommendations. It does you no good if you have the impression that I am an audiophile and then end up being disappointed by my recommendations.
So, here's my personal listening profile:
Good speakers or good head/earphones are where your money should be spent. There is very little difference between the players themselves. The source is digital so any differences in the sound is due to the player itself modifying and changing the source.
I think anyone that uses a discrete soundcard over intergrated audio is wasting money unless there is a specific feature the soundcard provides. There is literally no difference and blind tests done over and over and over and over prove this time and again. If you are listening at a PC, you would be better off investing in putting sound absorbing materials on your walls and creating an acoustically noiseless, listening environment.
A DAC does not improve audio quality, it changes it. It might change it so that you or another listener might like the tone or feel a little better, but the simple act of converting it from digital to analogue actually lowers the sound quality. Obviously, I am not a DAC fan, either. Analogue playback introduces analogue distortions. The "feel" is the opposite of accurate playback. The hiss of a record is not a quality I want and I can replicate and add it to my audio tracks with a digital filter if it matters that much.
Some people think they can hear a difference if they invest thousands of $$$, I don't. Can I tell the difference between a CD Rip to lossless FLAC and an .mp3 download from Amazon? Sure, but once you hit 320kbps on that .mp3 I would have to be told to listen for the difference to know that it exists. I don't believe there is 1 bit of difference provided by spending $1000 in a power cord for my home audio system and a I don't believe the sound reproduction in my head is improved when I stick pennies between my teeth when I listen. I generally listen to my .mp3 at the gym or working in the yard. My go to earbuds are JVC and RCA wraparounds that won't fall off my head. They are both about $20 at Target and I can tell which pair I am wearing because they do sound different. I have some Sennheiser headphones that I pull out every couple of months when I want to do some "serious" listening. They sound great but I regret spending the money because the difference just isn't big enough to justify the expense over a $40 pair of Sony headphones.
I hope this helps you get where I am coming from. You sound like someone that is willing to invest a little money to get the best quality within your budget and I think that's good. I literally cannot listen to more than about 15 seconds from someone's iPod and the stock earbuds. I would rather hum the tune in my head. My impression is that you are similar.
If you think we have similar listening styles:
Sansa Clip Zip + Senn 598 will make you happy. Optionally, it would be worth the extra $30-$50 to grab a Fiio amp.