All of your external drives are set to use permissions (as they all say "Ignore Ownership: No"). File permissions is probably causing the problem, especially if these drives were used on a different computer before.
On your Desktop, right click on your Band-in-a-Box hard drive and choose Get Info. If you are unable to see the hard drive on your desktop, please go to the Finder menu and choose Preferences, then under General make sure External Disks is checked.
Now press the yellow LOCK button at the bottom right of the window, and enter your password.
At the bottom, please check "Ignore ownership on this volume", then close the window. Now please try installing the update again.
Can you just copy it over to a new drive using the 2014 Mac ?
That would be my approach if the above doesn't help, or - backup the files, erase the drive, restore the files. I've never personally heard of iBoysoft, so I would be a bit leery of using it.