How to Encrypt Home Folder Located on External Drive

I have an iMac 5K with a 512GB internal SSD.  I decided to relocate my users' home folders to an external HDD due to their size (won't all fit on the SSD).
That part is working fine.  However, it has now dawned on me that I would like to encrypt those home folders in case that external HDD is stolen.  The problem, of course, is that by encrypting that external HDD, those users won't be able to login, since you can't login if your home folder is not immediately available.
Only solution that I read about is to have another user (with a home folder on the SSD) login first after startup and decrypt the HDD.  The would then allow the other users to login successfully.
Is that the solution I should go with here?  Or is there some other approach that will work better?  Or should I move my home folders back to the SSD and just keep the large stuff on the external HDD?

If your pictures, music, movies are not sensitive, you could relocate those to the external drive.

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    You should be able to format it for use with your computer using Disk Utility in the Utilities folder:
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  • How to Move iTunes Library on an External Drive to Another Computer

    How do you move your iTunes library (including all your playlists) if your iTunes media files—movies, TV shows, music, etc.—are housed on an external drive, rather than the local drive on your computer?
    The usual advice concerns copying media files from one computer to the next, e.g.:
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    http://support.apple.com/kb/ht1451
    Using this information, we can create a procedure for transferring both the media files that are on an external drive and the iTunes Library that goes with it.
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    2. You might want to note the number of music files, TV shows, etc. you have on the old system. Select View > Show Status Bar, then choose the “List” view, and this information will be shown at the bottom of the iTunes window. Also disable sharing, etc.; you may want to deauthorize the computer as well.
    3. Close iTunes on the old computer, dismount and disconnect the external drive(s). (Yes, this will work with media on multiple drives).
    4. On the new computer, close iTunes and delete “iTunes Library.itl” in the iTunes folder.
    5. On the new computer, Connect and mount the external drive(s).
    6. Open iTunes on the new computer. Choose Preferences > Advanced. Deselect (uncheck) both “Keep iTunes Media Organized” (because it’s already organized on your external drive, right?) and “Copy files to iTunes Media folder” (because the files are on the external drive). Then set your iTunes Media folder location to your media folder on the external drive and click on “OK”. (Note: don’t close iTunes after this step, because it will automatically reset your media folder to your local machine rather than the external drive).
    7. Choose File > Library > Import Playlist and choose the file you exported from the old computer. This will import all the media you had on the old system into iTunes (no need to manually move anything from the external drive). The import will probably take some time.  (If you see that iTunes is copying files, you probably messed up Step 6; you can stop it and go back to Step 4 without harm).
    8. After the import, you can check the numbers you noted in Step 2; if there is a discrepancy that bothers you, check out the scripts “Music Folder Files Not Added” “List MIAs” and at http://dougscripts.com/itunes/.
    9. When everything is satisfactory, you can recheck “Keep iTunes Media Organized” and “Copy files to iTunes Media folder” in Preferences.
    10. You may now want to enable sharing, sync iOS devices, etc. Also be sure to set up your backup strategies on the new machine (you *do* have backups of your external drive(s), right?). If you already had some media on your new computer and you want to incorporate it into the external drive, choose File > Library > Consolidate.
    11. Oddities:
    * iTunes Extras must be manually imported.
    * Some of my movies & TV shows imported as “Home Video”.
    * Mobile applications did not import (presumably because no iOS device was synced).
    * Books that were once handled by iTunes are now handled by iBooks and will not import (to let iTunes see them again, you’ll need to add them manually to iBooks, then choose File > Move Books from iTunes). Audiobooks import okay, but you may have to authorize your Audible account.

    Or:
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  • How do I sync music from an external drive

    I recently moved all my iTunes content including music to an external hard drive (multiple reasons: space, SONOS capability, etc.). In addition, I purchased a new iMac. I can wipe the nano, no problem, but how do I get music from the external drive that is not on my computer (but which iTunes will play via iCloud) onto the nano?
    Do I need to download everything back to my computer from iCloud and sync that way or is there some toggle I'm missing that allows me to load the external drive --> iTunes--> nano?
    Thanks!

    Jairy,
    You may need to run through the following steps:
    Once you've done that, follow the next set of steps to change your iTunes Media folder location to the new drive and then consolidate your library to the new location. This not only copies your audio and media files over, it also retains your ratings and playlists. Note: If you move your music and media to an external hard drive, you will need to have that drive connected to access your files. No matter what, it's always a good idea to have a backup of the media you have in iTunes.
    Open iTunes.
    From the iTunes menu, choose Preferences.
    Click the Advanced button in the Preferences window.
    Click the Change button in the iTunes Media folder location pane.
    In the Change Media Folder Location window that appears, navigate to the location where you would like your new iTunes Media folder to be created.
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    Click the New Folder button in the Change Media Folder Location window.
    In the New Folder window that appears, enter the name of the new iTunes Media folder.
    Click Create.
    Click Choose in the Change Media Folder Location window.
    Click OK in the Advanced window.
    From the File menu, choose Library and then Organize Library if using iTunes 9 or later. If you're using iTunes 7 or iTunes 8 for Mac, choose File > Library and then Consolidate Library.
    In the Organize Library (or Consolidate Library) window, select Consolidate files.
    Click OK.  Important: This action copies all of your music and media files to the new location. There must be enough hard disk space available to copy all of your music and media files.
    After the folder has been copied, locate your original iTunes Media folder, and drag it to the Trash. Important: Don't remove the iTunes Library files that may be in the same location as the iTunes Media folder. For more information about the iTunes Library files, see this article.
    Quit iTunes and then open iTunes once more.
    If you receive the alert "The folder containing "iTunes Library" cannot be found, and is required. Please choose or create a new iTunes library," you most likely moved the iTunes Library files. If this is the case, move them out of the Trash and back to where they were.
    If you can open and close iTunes without encountering the above alert, empty the Trash.
    iTunes for Mac: Moving your iTunes Media folder
    http://support.apple.com/kb/HT1449
    Cheers,
    Allen

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