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@Velocio
dicki, get a Cowon. Pretty much any one, though they keep their old players available for a long time, so focus on models in the last 12 months.
You don't need a headphone amp with a Cowon, though the Fiio's are wonderful and I do have one. I seldom use it though, the Cowon doesn't need it.
After that, FLAC is very good and "the way to go". Acquiring FLAC is mostly ripping your own collection or downloading illegally. There are few legal download sources of FLAC. If you need advice here on where to download from, PM me.
As for headphones, obviously open ones will leak a lot and offend people around you if you're on public transport, a plane, or in a café or something. I think the closed back Audio Technica cans are pretty nice: http://eu.audio-technica.com/en/products/product.asp?catID=5&subID=38&prodID=210
The problem with closed back being bass, and moving air in a sealed unit. The ATs do pretty well at this, the sound is not greatly affected by being closed back, and the performance is really sweet all things considering. They're good to use without offending those around you even in open plan offices.