Just jumped into portable audio with a FiiO X5. I have been happy with the Apple products to just provide sound when needed. For good sound I resort to my BAT amp and Dunlavy speakers.
I don't know what direction to go for head-fi. Over the ear, or IEM. One of the neat things about my reference setup is the way that the image is nailed down. Miles is in the wall and if he moves in the recording he moves in my listening room. Which style will provide that level of image and soundstage. My goal is to sit in the backyard with a cigar and beer watching the sunset, and have something approaching my reference system.