You'll probably need to remove those files from your mac (assuming you have a backup) and start over since it renamed/organized your stuff. You'll have to go into the options of iTunes and tell it not to manage your music then reimport. I can look at my Mac and give you the exact settings if you need me to.
man, I had like 200GB of audio I was bringing to this MPB. and I think the problem was I had to have itunes reorganize the music to go all in the itunes folder on windows. So I finally did that, and copied it to an external. I just gotta finish copying that from my external to this computer, and I should be good.
the first time I did it, I had the playlist, but the files weren't in the right location. hopefully this works tho.
one thing I dont like about mac, is on windows I have Office 2013, and on this shyt, I have Office 2011. and Office 2013 just completely shyts all over 2011. it's not even close.
Other than that, I should be good. my documents were all in dropbox, so moving them over was a non-issue. I got my photos moved over. Just gotta get this music and playlist, I'll be good.