I appreciate your advice, and apologize that I haven't had a solid block of time to dedicate to troubleshooting. So, the external hard drive isn't connected. I only use it for periodic back-ups, disconnecting it when not in use. I will apologize now for the length of this reply. Fair warning - it's a mess - and I won't be offended if you run & hide after reading it.
Details on a file I cannot recover - I copied the CD into iTunes, 2007
#1. Checking Edit/Preferences: "C:\Users\Dianne\Music\iTunes\iTunes Media"
#2: From Get Info: "file://local host/C:/Users/Dianne/Music/iTunes/iTunes Media/Music/Neil Young/Neil Young Unplugged/08 Helpless.mp3"
#3. the file doesn't exist on the computer - searching C:\ and then My Computer
A file I was able to recover - I purchased from iTunes, 4/8/2009
#1. Checking Edit/Preferences: "C:\Users\Dianne\Music\iTunes\iTunes Media"
#2. From Get Info: "C:\Geek Squad back Up 7.4.15\Dianne\music\iTunes\iTunes Media\Music\Nick Cave & The Bad Seeds\Abattoir Blues _ Lyre of Orpheus\17 O Children.m4a"
#3. There are three places I can find the track...see below.
In Explorer, I have two "Users" folders with different dates. One dated 06/12/2016, the other 7/11/2015 (which is close to when my prior laptop was dying).
The 6/12 "Users" folder has iTunes and iTunes Media folders at the same level.
The My Music\iTunes\iTunes Media\Music path has just 9 items...artist folders.
The My Music\iTunes Media\Music path has 163 items, combination of artist folders and individual tracks.
- The 7/11 "Users" folder has only My Music\iTunes\iTunes Media\Music path...and has the same 163 items...
- The "Libraries > My Music" shortcut appears to be set up like the 6/12 Users folder - there is an iTunes Media folder on the same level as iTunes, except the My Music\iTunes Media\Music path yields 178 tracks - no folders.
O Children.m4a is visible via both "Users" folders...but not the "Libraries > My Music" shortcut.
- 6/12...OS(C:) \Users\Dianne\My Music\iTunes\iTunes Media\Music\Nick Cave & The Bad Seeds\Abattoir Blues _ Lyre of Orpheus\17 O Children.m4a (the Users folder dated 6/12) - in Properties...location is same as shown here
- 6/12...OS(C:)\Users\Dianne\My Music\iTunes Media\Music\Nick Cave & The Bad Seeds\Abattoir Blues _ Lyre of Orpheus\17 O Children.m4a (the iTunes Media folder is also avail. on the same level as iTunes...) - in Properties...location is same as shown here
- 7/11...OS(C:) \Users\Dianne\My Music\iTunes\iTunes Media\Music\Nick Cave & The Bad Seeds\Abattoir Blues _ Lyre of \Orpheus\17 O Children.m4a (Users folder dated 7/11) - in Properties...location matches #2 above from Get Info.