Cart Before the Horse: Signal Path Help Please

Hello all -

Short version:
What is the best way to get FLAC files from an external HD --> DAC --> integrated -->Speakers?

Long Version:

I have been digitizing my CDs, building on my extensive Pink Floyd Bootleg collection and purchasing some HD Audio. Currently all of this is housed on an external FireWire HD - with me swapping files to my Laptop as I feel like it. I also listen to a lot of Spotify to discover new music (much of which I then purchase on CD, LP w/ Download or HD).

I'm trying to figure how best to tie all of this together in the cleanest AND user friendly way. For instance - I'd love to be able to rip CD's or Download HD to my laptop and then wirelessly transfer to an external HD and then be able to control that via my iphone. Or be able to do spotify direct from a magic box, etc ...

I hope this isn't too wide ranging a question and there is an obvious way that I am missing.

So I'm building my new system in somewhat of a convoluted order. At this point i have:
- Primare i30 Integrated Amp
- Primare CD31 CD Player
- Music Fidelity m1DAC A
- Pair 1 Meter XLR interconnects
- .5m Fairly nice TosLink Cable
- 1st Generation 40 gb appleTV

On the Way:
Orbit Turntable from KickStarter (Just for fun!)

Left over - to probably be upgraded (but that is a whole other thread!)
- 1 Pair B&W 685s
- 1 Pair Kimber In Wall Bi-Wired Speaker Cables (25') Decent at $2.75/ Foot

thank you!
Septemous