Hi James - Thanks for the tip! I tried the Redownload procedure on a couple of files in my library that were listed as purchased in April of 2012. When I clicked the download icon the files were restored, still protected. Also the date of purchase changed from April 2012 to January of 2007. Apparently I forgot that the library had been refreshed in 2012 (probably when the Shuffle I originally purchased died and I replaced it with a Nano?). I think I probably need to try iTunes Support again in hopes I can find someone with a big enough hammer. Thanks very much for your time and consideration.
David