I recently purchased my first Mac and I am attempting to use iTunes for the first time (I've been using Ephpod and Anapod on my Windows PC). Like a lot of Windows PC users, I have my music organized in a directory strutcture where I have 100's of folders each containing multiple mp3 files. For example, I have a folder called "Rap" - inside that folder are random rap songs by random artists. I have similar folders for Rock, R&B, etc. I also have tons of folders that are my actual albums that I ripped from CDs that I own. For example, I have a folder called "Coldplay X&Y", a folder called "Keane - Under the Iron Sea" etc. The way I handle this on my Windows PC is that whenever I sync my ipod, the software automatically creates "playlists" on my ipod based on the names of my directories. In other words, I had playlists on my ipod called Rap, Rock, Coldplay X&Y, etc. This worked great for me because every time I added new songs to any of those directories on my PC, they would automatically get added to my ipod on the next sync. iTunes appears to work completely differently and I'm not quite sure how to best utilize the program to suit my needs. Obviously for playlists that are actually just full albums (Coldplay X&Y, etc.), those will never change since I never add songs to them; however, I am constantly adding new songs to my "genre" playlists like Rap, Rock, etc. and I want to make sure that those new songs make it on to my ipods when I sync them with my Mac. How would you guys recommend I handle my music via iTunes? I'm very open to suggestions since I'm trying to fully convert from a Windows user to a Mac user, but I also want to make sure iTunes can meet my needs. Any help is greatly appreciated.