What music is best for life in a tiny box?

The US Navy is sending me to Japan. My family is going to stay here in the States. That means I get to live on the ship! Imagine a tiny stateroom; that will be home for the next 2 years.

So..obviously my vinyl collection will stay home. I am thinking of going completely medialess digital.

What do you recommend for:
DAC (are there any that can read from an external hard-drive?)
Headphone Amp?

Portable media player (when i get away from the ship. Must read FLAC, no Apple! :) )

Since my system will be so small, I think I can afford somewhat better gear. I am thinking in the $2k range.

Your thoughts?
I think that you might have better luck with this question on Head-Fi. A couple questions that come to mind. Do you need the amp and headphones and digital player to be portable? Do you need your headphones to block out noise? When you say a DAC reading from an external hard drive, do you mean without any computer involved? Do you have tube vs solid state preferences on the amp?

For $2k you can put together a great headphone set-up.
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Some ideas, with the core being a computer and a real decent DAC:

Decent netbook with large solid state drive for media storage ($500)
CEentrance Dacport usb DAC/headphone amp ($400)
Sennheiser HD 600 Headphones ($314.95 on Amazon)
Etymotic ER4 earphones for when sound isolation is needed -or different flavor ($299)
Audioengine 5 powered speakers when you have had enough of headphone listening! ($325)
Total: $1840
Storage these days is compact and cheap: since you can afford some decent hardware, I should think you'd want to use media in lossless format like FLAC, not MP3. For the goods on the computer-based front end: computeraudiophile.com (though it is somewhat MAC-centric).

Thank you for your service.

I'm in a similar situation, but only for 5 months. I purchased a Cambridge Audio DACmagic from Audio Advisor, and paired it up with my 90's vintage Headroom Supreme amp and pair of Sennheiser HD600s. I've been very pleased with the audio quality of digital music played from my MacBook (but if you are new to hard-drive based audio, make sure you import music at a respectable bit-rate).

The new DAC has made a huge difference in listening to music from the computer...I found myself listening for hours, with no fatigue.

I also purchased a pair of Audio Engine model 2 self-powered speakers, for casual listening when I don't want to be tied to headphones. Just got them yesterday; very impressed with build quality, and they are nice and compact. Initial impression is very favorable, but I'll need to break them in to make an accurate assessment. But if you are in the market for an inexpensive ($200) compact speaker, check 'em out. The model 5s mentioned in Arni's post also get rave reviews, but they may take up a little too much desk-top real estate for ship-board living.

Good luck on your tour in Japan.