The speakers and/or headphones along with the source audio is more important than the player imo.
I used to listen to lossless files, but they take up so much room, and I didn't notice a huge difference between them and 320kb/s mp3's.
I use Yuin PK1 earbuds. Earbuds have always felt most comfortable to me, so that's what I stick with. PK1's with a simple portable headphone amp (i use a fiio e5) and I'm happy. For a player, I just use my zune 80gb.
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