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I don't know for sure, but most likely the problem is that iTunes keeps songs in AAC format, and the Garmin wants them in MP3 format.
If that's the case, then what you need to do is this:
in iTunes, build a playlist of the songs you want to export. Click on that playlist to show the list of songs Click on the first song in the list, then hold SHIFT and click on the last song in the list so they're all highlighted. Select the menu option "Make and MP3 copy". Apple keeps moving this option, so you may have to hunt for it, depending on the version of iTunes you have.
This should leave the nice-quality AAC versions alone, but also make MP3 copies of each song. Copy the MP3 files to the SD card and try that in your Garmin.
your 660 uses a micro sd card located in the battery area...see page 5 of your manual HERE you can download your manual from that page if you do not have one...see pic below for the location of the micro sd card
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