haha, no worries. I feel a deep and intense sense of hate and dread at the thought of anything remotely related to microsoft in my house. apple works for me.
FLAC/ALAC doesn't matter, lossless is lossless. Either way though, for whatever your OS choice is, there are good audiophile players that handle the playback way better than iTunes (which natively has a bloody terrible conversion) or media monkey.
Then its a matter of finding a good external DAC. I prefer an optical out from the computer, USB is prone to noise from hard drives and whatnot. I use a cheapie Muse eBay job, but it runs 4 TDA chips which for the $60 it cost has a really nice sound.