Q: Best alternative for locating lost library & playlists?

You are the one who is going to have to see how you have your iTunes collection structured and determine which option you elected to use when keeping things on the external drive.  It is possibel to have it so just media are on the external drive.  It is possible to have it so the whole library is on the external drive.  Check your file and folder strucure and compare to the links below.  Typically keeping just media on the external drive iwll not include seeing a library file (library.itl) on the external drive but you may have put an older copy there.  By checking file modification dates it should be possible to determine which of your library files is the newest. 

What are the iTunes library files? - http://support.apple.com/kb/HT1660

More on iTunes library files and what they do - http://en.wikipedia.org/wiki/ITunes#Media_management

What are all those iTunes files? - http://www.macworld.com/article/139974/2009/04/itunes_files.html

The .xml version is not your library file.  It is a copy of the library file in a different format so it can be read by other applications.  Typically it gets updated along with the actual library file though.

iTunes 9 [and later]: Understanding iTunes Media Organization - http://support.apple.com/kb/ht3847

Use Spotlight to search for files ending in .itl.  As far as I know, the iTunes library is the only one that will.  You should be able to find one more recent than two months old.  If you cannot then you can get the library.itl file from Time Machine.  I have never used Time Machine so I can't help with details.

Double-clicking on an .itl file opens iTunes, but not necessarily the file that was clicked on. To check the contents of an .itl database you need to connect to it after holding down Option(Mac) or Shift(Win) as you click the icon to start iTunes and are prompted to choose or create a new library.

If you know where the active library file is then this is the easiest way to restore a recent backup.

Empty/corrupt library after upgrade/crash

Hopefully it's not been too long since you last upgraded iTunes, in fact if you get an empty/incomplete library immediately after upgrading then with the following steps you shouldn't lose a thing or need to do any further housekeeping. In the Previous iTunes Libraries folder should be a number of dated iTunes Library files. Take the most recent of these and copy it into the iTunes folder. Rename iTunes Library.itl as iTunes Library (Corrupt).itl and then rename the restored file as iTunes Library.itl. Start iTunes. Should all be good, bar any recent additions to or deletions from your library.

See MusicFolder Files Not Added and Super Remove Dead Tracks for tools to catch up with any changes since the backup file was created.

tt2

turingtest2 wrote:

 

Double-clicking on an .itl file opens iTunes, but not necessarily the file that was clicked on. To check the contents of an .itl database you need to connect to it after holding down Option(Mac) or Shift(Win) as you click the icon to start iTunes and are prompted to choose or create a new library.

OP's first post: "I'm assuming I need to relocate my Library after holding down the OPTION key"  and I am assuming "tried opening them through iTunes" in the OP's second post was also referring to that.

In the Previous iTunes Libraries folder should be a number of dated iTunes Library files. Take the most recent of these and copy it into the iTunes folder.

Or as the OP inquired and I was discussing in my last post, get a more recent version of a good library file from the Time Machine backup, and start up from that.  This is immensely preferable to using the old library file from an update unlesss the update really was done very recently or there have been no changes (including not playing any music if playcount is important) since updating the iTunes application.

Apologies for failing the comprehension test.

I focused on the phrase "I am still getting a library that is over 2 months old. " which made me suspect that the OP might not be successfully opening alternate libraries at all.

tt2

Download Easyfind. 

http://www.devontechnologies.com/products/freeware.html

Tell it to search your drive for files with .itl

If it doesn't find the one you want/need then it is history.

The .itl file (and its sister .xml) should be located in whatever folder you use for your iTunes library.  I have 4 libraries so it is not a given, but usually it is Home > Music > iTunes

Make a backup of your drives in future.  If nothing else, make a backup of the .itl file, though most people lose their library file by the whole drive dying, so it makes sense just to maintain a regular backup of your whole drive.

You have only one current library.itl file (unless you use multiple libraries).  Go into the iTunes folder periodically and duplicate it (Finder > Duplicate  but I also use a 7 year old system so they may have changed it).

Every time you update iTunes from one build to another the current .itl file is placed in the Previous iTunes Libraries folder and a new one generated from it. The new one is flagged with the current build number which is one of the reasons downgrading iTunes is tricky. You can of course manually backup the .itl database as often as you wish, as well as putting automatic backup schemes in place. Hmm, of course if your library was originally created before iTunes 9 on a Mac the database file would have been called simply iTunes Library without the .itl extension. I suppose it might just be work doublechecking.

To backup simply the copy from the current source folder to a backup location of your choice.

When you say "I have many, is there one save that saves them all" you surely have only one or two active libraries? One is sufficent for me to look after all my media and the family's devices though I do occasionaly create test libraries to illustrate or test things for here.

tt2