Hey Jeff,
I'm a MAC user and new to Brennan also. I found an easier and quicker way to import files from my MAC or most any other source quickly and easily. This also totally negates the use of moving a USB stick back and forth.
The organization of the files must be as Paul stated. I've found that iTunes formats correctly but that my not be the case for you. Who knows.
You also need to use the Web UI to do this. It's just much easier. Wire in via ethernet if at all possible and you miss any issues with Wifi. AND unplug the Wifi dongle if you do this!!
1. In the lower left panel of the Web UI there are 4(?) tabs. The one to the right says UPLOAD. Click on that and you can Browse your computer/system to your music files.
2. Organization = Artist folder > Album folder > Song [Note that all songs must be preceded by 01, 02, 03, etc. This is how the organization works or else it's alphabetical] I'm sure you've discovered this already.
3. I also discovered it's best to do this one ALBUM at a time. You can load a bunch of them at once but it REALLY SLOWS THINGS DOWN!!!
4. This WILL NOT change the file type of the music unless you are transferring WAV files. My MAC files are AAC lossless (maybe mp4) and some MP3.
Brennan will only convert WAV files to FLAC.
I hope this helps. It was a revelation to me.
Randy
Brennan Support.