Hello Everyone,  

In an effort to make your iTunes pruning efforts as painless as possible, I
am listing the steps I personally followed below:  

How To Remove Broken or Dead Entries from Your Computer's iTunes Library

The following steps will let you isolate/display only the broken or dead
Music entries in your iTunes Library.  After doing this, you can either
repair or delete these entries.  

NOTE 1:
This document assumes that you are familiar with the basic functions of
iTunes.

NOTE 2:
Before you begin, make a complete backup of your entire iTunes Library.

NOTE 3:
This document assumes that you know how to create a Smart Playlist.

NOTE 4:
This document is based on iTunes 11.3.

NOTE 5:
Before you begin, make sure that there are no iOS devices attached to your
computer.  

NOTE 6:
>From the iTunes View menu, be certain to hide iCloud Music purchases.

>From within iTunes do the following:

1.
Create a standard (static) playlist named "All Live Files".  

2.
If using the Sidebar, select the Music Tab.

3.
Drag the entire contents of your Music Library to the "All Live Files"
playlist that you created in Step 1.  
Only unbroken/live/intact Library entries will be copied to the playlist.  

NOTE 7: 
Depending upon the size of your Library, it may take several seconds for the
items to be copied.

4.
>From the File menu, select the New Smart Playlist option.  A dialog box will
appear.

5.
Place a checkmark in the "Match All of the Following Rules" item.

NOTE 8:
This Smart Playlist will contain three rules.

6.
Set the first rule to read
"Playlist" "Is" "Music"

Set the second rule to read
"Playlist" "is not" "All Live Files"

Set the third rule to read
"Location" "is" "on this computer"

7.
Uncheck the "Limit To" checkbox.

8.
Place a checkmark in the "Live Updating" checkbox

9.
Click the OK button and name the playlist Missing Files in the resulting
name edit field.  Upon pressing the Return key in order to create the Smart
Playlist, you will see a list containing only those items which were not
copied to the "All Live Files" playlist.

AT this point, you can either attempt to repair the broken links or delete
them.  I strongly suggest that you verify that these items are, in fact,
dead, before deleting them.

Should you choose to delete the broken entries, I suggest that you first
edit the Smart Playlist by un-checking the Live Updating option.  This will
allow you to delete items either one at a time or all at once.

Good Luck and Happy Pruning.

Mark

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