[osxcode]

What I do is format a USB stick (largest memory stick I can find) and create folders on the memory stick. One for Rock, Soul, Modern,...etc... Then I make subfolders for the Artist within those categories. Then, I just drag the songs for the appropriate artist, out of my iTunes widow directly to the folder the songs belong in. All of my files are high quality 320KBS per file, if you have a Hi-Fidelity system, 320KBS is better than CD quality for the most part and theres no loss of definition. I wouldn't convert files from one thing to the other, sometimes you lose quality in the process.

Once I put the USB stick together, I just copy things on and off the usb stick and when I am ready to upload the new stuff to the car, I delete the entire collection and re-import the USB stick. There doesn't seem to be a way to only import new things.

With BMW's new Nav systems (as of 2013 refresh) the larger hard drive and the speedier cpu of the nav/radio unit is just outstanding. I can upload my entire USB stick of high quality soundtrack in only minutes versus having to wait for a longer road trip to do the import. In my older 2011 550i, the process would take up to 45 minutes.

Dragging the songs out of iTunes is very easy and requires no conversions, not to mention, you keep the quality of the given track.