I'm a windows kind of guy, so I know squat about Apple & personally do not care for iTurnes cuz it is so inflexible & does not have the best sound quality. My current set-up is an 8TB Server > MF V-Link 192 > Schiit Gungnir DAC > C-19 > Rotel RB-1090 > DIY 2-1/2 way Towers w/ 2 HSU subs
For a windows based laptop, see this link for some good set-up info to maximize performance.
http://www.native-instruments.com/knowledge/questions/847/Windows+7+Tuning+Tips+for+Audio+ProcessingI put all my files into FLAC format. It is 100% lossless & about 30% smaller in size than other losless formats.
If find your memory is not big enough you can get a small portable USB HD for less than $100.
You run a USB cable to your DAC if it has a USN input. If your DAC does not, you can get a USB to SPDIF converter. Run a USB cable to the converter. Then run a coax digital or TosLink (optical) to your DAC. I recommend the Music Fidelity V-Link 192
http://www.audioadvisor.com/prodinfo.asp?number=MFVL192I use AISO4ALL v2 as my output driver.
I use dBpoweramp for ripping. It imports all the metadata & cover-art automatically & will auto-correct any errors.
I use Foobar to manage & play all my music.
I think the Drangonfly is probably the best value out there right now in DAC's. It can easily be used for headphones or in your main system.
As always,
JMHO YMMV