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[RGlideKid]

Not having an iPod or iPhone to connect to my new 2015 CVO Road Glide Ultra, I've been struggling to get my almost 3,000 song MP3 collection to be read from an SD card by the USB connection and the Boom Box.
After doing a lot of research about needing to download this app or that executable file, I was almost ready to give in.  It just seemed to be needlessly complicated.  I've tried my Sony 16GB MP3 player that the Boom Box will read just fine...except for playlists and genres, which is how I divide up my music into more usable and playable chunks.  I've tried different combinations of SD cards and USB readers, but nothing seemed to work...until now.
Before you go any further, I'm using iTunes and a 32GB SD card with a simple USB 2.0 adapter (Walmart).  I tried using a 3.0 USB to SD adapter and got nowhere.  If you're using a PC, the menu items I talk about below will be different but not much.  I'm told the process will still work for you.

Here are the steps I used:

In iTunes (on my MacBook),

1)go to the menu item iTunes>Preferences>Advanced (Tab)
2)if one or both boxes at the top aren't checked already, select both boxes that say "Keep iTunes Media folder organized" and "copy files to itunes media folder when adding to library".  If these two boxes were already checked, skip down to step 3a.  Otherwise proceed to step 3.
3) above these two check boxes is your media folder location box.  You can change this to whatever path you want.  This is where iTunes puts an exact copy of your library.  You can either specify a custom location, or just select the "reset" button to the right that will enter the default location.  Either way, remember the path shown in this box so you can find the folder later on!

NOTE:  You are creating an exact duplicate of your entire music library, so you need to make sure you have the disk space available (either HDD OR SSD) to be able to do this!  Hey, you can always delete the copied library later if you need the disc space.

3a) If you already had those 2 boxes checked from step 2 above, you will likely already have the duplicate library on your computer.  If you can find the library folder, then skip to step 5!  If you can't find it, go back up to step 3 and it will tell you how to find your folder.
4) click "OK" at the bottom of this window.  Your computer will now begin making the duplicate library.  Also, since you now have the boxes checked, any time you add new music to your computer, I believe it will be added to your duplicate folder as well.  This takes time, so if you add music a lot to your library and don't like waiting, just go back in and uncheck those two boxes and that will stop the future "syncing" activity.
5) Once the duplicate library's been created, find it and open it in your Finder (Windows Explorer) window, then select all the albums in the folder (or just the ones you want to copy to your SD card for the bike), and then copy them to the SD card.  I formatted the SD card to FAT32 and this process worked fine for me.
6) When the copying is all done, plug your SD card into your USB card reader, then plug this into the connection on the bike.  Remember, the more info that you put on the card, the more time it will take for the bike to read all of it and show it to you on the boom box menu, so don't panic if it initially takes a minute or two the first time.
I suppose you could get a faster reading SD card, but then the information's being piped thru a 2.0 USB connection, which will choke the speed of information transfer down from the card to the radio anyway, so...

I'm not sure why this process works when so many others I've tried don't, but it does.  I found it in a search for how to back up your iTunes library and that led to a link that showed how to copy that backup to an external device.

I still don't know if the Boom Box will find playlists using the above approach, but it does find all the genre's your songs fit into.  Most of my genre's are ones that I created from scratch because the default genres are just too general and not specific enough for me sometimes.  I have about 2 dozen genre's that I've created to simplify music selection as much as possible, which ain't easy when you have almost 3,000 MP3's to choose from.  Since I have all the Beatles on MP3, I even gave them their own stand-alone genre.

In iTunes, it's easy to select one or even multiple songs and then go in and edit the existing file information on the Genre to reflect one you want.  You don't have to stay with the one showing in itunes.   iTunes then remembers these changes and somehow it gets transferred to your SD card, and the Boom Box can read them just fine.

If you have questions or comments or other ideas, let me know.  I don't own any USB memory sticks, but I do have a boatload of SD cards, so that's what I was using.  I would imagine that a USB stick will work just as well using this process. 

Hope this works for y'all!