Downloading iTunes files to an external HD

The iTunes Media folder location only refers to where iTunes places imports from CD, but there is a known bug whereby iTunes fails to remember your change to a different location. The problem has been outstanding for a long time and it doesn't look as though it will be fixed in the near future.

However, if you buy music from the iTunes Store, iTunes will download the files into the appropriate location because it isn't dependant upon the Edit/Preferences/Advanced setting. That location should be "your choice of parent folder (i.e. your external drive)"\iTunes\iTunes Media\<artist name>\<album title>.

Likewise, any music that you buy from other online sources, such as Amazon or Bandcamp, will be where you put it and again, that location is independent from the location used for CD imports. For example, you add those purchases to the folder of your choice, then use iTunes' top bar menu File/Add Folder to Library to add the contents of that folder to your iTunes Library.

So you only need to think about the location setting when you import from CD. On the (now) rare occasions when I import from CD, I usually forget to change the setting to my new location, import the CD, remember the issue, get frustrated and then move the files to the correct location and finally tell iTunes where to find those moved files. (Alternatively, I delete the CD rip, change the location and then re-rip the CD (again, with a certain degree of frustration.)

See my response to your other thread Getting iTunes to display all the music i… - Apple Community.

There is a now 4 year old bug in iTunes that, at least for some users, seems to stop the media folder preference from being saved properly. See Make a split library portable - Apple Community and put your library in a shape that isn't affected by the issue, and is easier to backup and move around in future.

tt2