Ahhhh, I'm losing my mind! I'm getting a new iMac in a few weeks. It'll be my first ever Mac system. I'm learning everything I can about it now before it gets here so I'll have a head start. As such, I'm switching to iTunes as my main media player. Problem is, I have a ton of music, videos, pictures, etc already. I want to let iTunes do it's thing to my music, keep it organized and everything. This is coming from being very very anal about my files and path locations. I want to know how to organize my music so iTunes will see it, keep it updated if I add new files, you know, like Windows Media Player watched folders. So I did a bit of googling, and manually organized my files like so: .iTunes Media ..Audiobooks ..Automatically Add to iTunes ..Movies ..Music ..TV Shows And so on. Then I set iTunes Media Folder Location to that folder: "C:\Users\LayzieGTP\iTunes Media". I checked 'Keep iTunes Media Folder Organized', clicked okay... and nothing happened. I'm not sure what I expected to happen, I guess I thought it would import my songs and videos and stuff into iTunes, but it didn't do anything! My library shows it's empty. Hrrmmmm... So, I'm sure somebody here knows what I'm doing wrong, and I'm sure it's simple, but be gentle... I'm new to Apple. On that note, I know I can go to File>Add Folder to library, but that folder isn't 'Watched'. If I delete files manually, rename files, move them, or add new ones, they aren't updated in iTunes! It seems sloppy at best. Plus, if I then download new music, or add new stuff within iTunes, they go to the Media Library location >.< Heeeelp! I give iTunes complete permission to control my media, and it doesn't want to!