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...I have nothing now and the budget needs to fit preamp, amp (is this needed with a preamp?), speakers, cables, turntable etc to get started.
The amp is what drives the headphones, the preamp essentially controls input signal strength for whatever gain the amplifier has. If you don't need a headphone with this system, get an integrated amp (has a preamp and amplifier in the same box), otherwise some devices have a DAC, headphone amp, and preamp all in one box - pair this with a power amp and you're good to go with whatever headphones and speakers these can drive.
And yes, the points raised about using analogue are worth considering. As well do check the other forums recommended as they are more up to date with speaker gear and their (used) prices. In any case, for up to $4,000, here's a general idea of what I'd get:
Source : Emotiva ERC-2 (available as refurb, new one coming up soon) / Musical Fidelity M3CD* / used Cayin CD23T
Amplifier : Emotiva A100 / Musical Fidelity M3i* / used Musical Fidelity A1 in great condition, Unison Research Unico
Speakers : Focal 607V, on sale here http://www.musicdirect.com/p-41246-focal-chorus-706v-bookshelf-speakers-pr.aspx
Cables : Order from Blue Jeans Cable, I don't think you'd spend more than $60 on analog interconnects and speaker cables
*I've listened only to the MF's, but they're about 4x to 5x the price of the Emotivas. I'd personally gamble on the Emotivas I haven't heard, based on the great feedback about their sound, than blowing 3,000 on the CDP and amplifier, unless that three grand is like my surplus quarterly income