Why does my music disappear every time iTunes updates

I have music disappearing at an alarming rate out of iTunes. When I moved from my Sony to the MacBook, I complained that I have more then 20 days of music missing.  I am updating a new iPhone and 99 songs are now missing (songs that were present last week).  These were my top pick songs with a combination of downloaded CD's and downloaded purchase.  The name is listed and all of the information, but iTunes can not locate the music.  I also have digital music "skipping" in my playlist.
It seems that most of the music that is missing are CD's that I downloaded, but there is a good amount of purchased songs also missing.  I also have digital booklets and videos missing.  I have only used iTunes since the early 2000's.  I do have a lot of this missing music on both of my sony computers, but I have not updated iTunes on them in a long time.
How can I get my music back?  Most of the CD's I have gotten rid of because I don't see the point in waisting space.  I really do not want to return to a CD system for my company and personal use.  I enjoy using my iPhone for transporting my music from location to location.
Thank you,
E

Hello E
Start with finding the path where the songs are on your PC by right clicking the songs that are missing in iTunes and click Get Info. You should get a window that pops up and in the Summary tab; the path will be there. Then navigate to where it was and see if the files exist. Other than that you can try to search your computer to find those files. Checkout the articles below for tips on finding the missing music, also if some of the tracks are downloaded from the iTunes Store you can download the tracks again by deleting the missing tracks from iTunes and then navigating to the purchases section in the iTunes Store to download them again.
iTunes: Finding lost media and downloads
http://support.apple.com/kb/TS1408
Download past purchases
http://support.apple.com/kb/HT2519
Regards,
-Norm G.

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