Warning, first world problems incoming....okay, so I have 128GB hard drive on my rMBP being the base model. It would seem my PC has more than that or I'm at the limit already. With my music in FLAC it takes up 83.5GB of space, I have about 15GB of movies in mp4's, and I'll need space for other things (I assume downloads from the Mac App Store use this memory as well?). So basically transferring everything I have, as it is, is out of the question. My music I need transferred period so I can sync my iPhone with my rMBP, I think I can start syncing my iPad with it as it has no music, just apps and I've transferred purchases from both my iPad and iPhone to my rMBP. I've already decided my work files, even though small, will go into SkyDrive. I'll have to download Steam for Mac and install my two games via that. Basically, I'm asking what should be the priority for my transferring? Or the best way to do so? I'm having trouble installing the newest version of iTunes on my PC, there is no old version to open and when there was, it was met with an error, it keeps telling me I'm missing a file. Assuming I get iTunes running on my PC again, would the transfer client transfer all my music from iTunes on my PC over to iTunes on my MAC as Apple says it should? The music is the biggest issue for me really, my iPhone is currently my music listening device. Should I keep both my rMBP and PC for separate purposes?