Longer answer than ScotteLip, but with a few of the details described. Hope it helps. Regards, W.
How to make iTunes play nice with Ford Sync v2.x: Music and playlists.
Ford Sync is a Microsoft product, and as such, it takes a little work (and patience) to make it work properly with your Mac-based music collection. However, with a bit of effort, it's very easy to set up your USB flash RAM drive to work nicely with your Ford Touch Sync software.
First, format your flash drive as a "MS-DOS (FAT)" drive. Do this by running the Disk Utility application in your Applications > Utilities folder. Click on the USB drive on the left side of the window, click Erase, then choose the format MS-DOS. Give the drive a short name that does not contain spaces. For example, "USBMusic."
It turns out that Sync can find music that is buried in folders, even if the folder names have spaces in them, and even if the file structure is the same as iTunes. This is very helpful, since it means you can use an entire iTunes library as the source of your music. The only downside to this approach is that it wastes a little bit of USB RAM space (about 1 or 2 songs' worth).
Now we will prepare our music files for the vehicle. I haven't done an exhaustive list of supported audio file types, but AAC and MP3 are definitely acceptable. (I don't know if there is a maximum or minimum allowable bit rate, but I prefer AAC at 256k, which is helpfully called iTunes Plus by Apple.)
You will need to convert all of your music to one of the acceptable file formats. Launch iTunes. Choose iTunes > Preferences > General. Click Import Settings, and choose your format. If you need to rip file from a CD, do that first. It's simpler if the files are already in iTunes.
Quick note: Do NOT transcode from one lossy format to another. In simpler terms, if you have AAC music or MP3 music already, DO NOT CHANGE THESE FILES. I keep all my music in Apple Lossless format, so I have to compress the files first. Select the files that need to be converted, then choose File > Create New Version > AAC version (for example). iTunes will get to work changing the file format to your preferred file type.
Once this process finishes, create a new folder on your Desktop called "MusicForSync" or some similar thing. Drag the converted music (and any files you didn't need to convert) from the iTunes window directly into this folder. This process is a bit of a pain. If you have two files with exactly the same file name, iTunes may simply ignore your WHOLE drag command. (Some versions allow the Finder to tell you what went wrong.) This is a pain. I usually pull about 30 files at a time, but you can try the whole batch, or do a binary division attack. In any event, if you run into a name collision, figure out which file is causing the problem, then rename the file in the MusicForSync folder to something that won't collide.
At this point, you should have an iTunes library that contains 2 copies of many of your songs, plus a Desktop folder containing another copy of your music, but all in MP3 or AAC format. I delete the newly converted files from iTunes at this point, but you may prefer to keep them for the future.
Now, quit iTunes, then re-launch it while holding down the option key. iTunes will ask you if you want to create a new library ("Create Library"). You do. Name the library something like "FordTunes" and save the library on your flash RAM drive. Make sure you have iTunes set to copy the files to the iTunes library (iTunes > Preferences > Advanced > Keep iTunes LIbrary Organized). This is important.
Drag the folder of music you made ("MusicForSync") into the new iTunes library. iTunes will (slowly) import the converted files, copying them to the USB drive. This takes some time, since flash drives are nowhere near as quick as hard drives. When the process finishes, you should have a complete iTunes library file structure on your USB drive. Delete the MusicForSync folder and its contents.
Now, you can go about making playlists in this library, both manual and "smart" types. Give these playlists short names WITHOUT SPACES. ("80sMusic", "Metal", etc.) When you're done, you need to export each playlist to the USB drive. It's easiest to put them in the directory containing your music file folder. In the current example, that would be "/Volumes/USBMusic/FordTunes Library/iTunes Media." To export, choose File > Library > Export Playlist…" then choose the proper location and playlist name.
Now that you have exported your playlists, we must fix them so Sync can read them. You'll need a text editor of some type. TextEdit is fine, but I prefer BareBones' TextWrangler myself. It's free, very powerful, and (did I mention) free. http://www.barebones.com/products/textwrangler/download.html
Find the playlist you exported (for now let's assume "PinkFloyd.m3u") and drag that file onto the TextWrangler icon. Press Command-F (it used to be Apple-F) to open the find/replace window. First, we will make all the path names relative to the location of the playlist file. Find the file path of the first song, which will be something like "/Volumes/USBMusic/FordTunes Library/iTunes Media/Music/Pink Floyd/.…." Highlight everything up to (but NOT including the slash before the word "Music" indicating the Music folder. The next path component should be the band's name. Copy this string and paste it into the Find field of the Find window. In the Replace field, enter a single period. Now click Replace All. Your library should now have file paths that read "./Music/Pink Floyd/.….."
Next, we need to make the proper front slashes into Windoze back slashes. In the Find window, erase the path information an put a solitary front slash ("/"). In the replace field, remove the period and enter a back slash ("\"). Click Replace All.
Now, paths should look like ".\Music\Pink Floyd\…."
At this point, we need to save the file to the USB drive using Windoze line terminations (CR/LF). Choose File > Save As, then ensure that the new playlist file will be saved on top of the old file (chose the same directory and file name). Choose the Line Breaks drop-down and select Windows (CRLF). Make sure the Encoding is UTF-8. Click Save and let the program overwrite the old file. Do this for each playlist.
Now, we must remove the Macintosh data fork file names, or else we get a bunch of empty playlists with names starting with "._". So, take a trip to Terminal, which is an application in your Utilities folder. At the prompt, type "cd /Volumes/USBMusic/FordTunes\ Library/iTunes\ Media" . (Note the backslash before the space, telling the shell to escape that space (that is, escape from considering it a break in the command)). Now, type ls -la. You should see a bunch of superfluous playlists like ._PinkFloyd, etc. Type rm ._*.* and press return. that will remove those files from the directory.
That should be all you need to do. Quit iTunes and TextWrangler, then eject the USB drive. Put it in your Sync vehicle and let it index the drive.
In the future, you can stick the USB drive back in your Mac, option-launch iTunes to select that library again, add or remove songs as you like, then re-export and re-tune your playlists.
