How to automate the conversion of an iTunes library in windows to mac

Question

If I import a windows iTunes library it does not have all my playlists in the mac version. How can they automatically convert the library to a mac one?

Answer 1

Simple definitive steps to transfer your Windows iTunes Library to Mac.

It will preserve playlists, play counts, [most] album artwork etc.
It doesn't require extensive knowledge of either Mac or Windows - even the 'difficult' bits ought to be easy to follow.

(For a more 'hardcore' method, using sed, see my answer at https://apple.stackexchange.com/a/157670/85275 )

It also includes a step usually missed in the online guides…

1. First, make sure you have prefs > Advanced > 'Keep iTunes Media folder organised' checked.
   If not, then go to File menu > Library > Organise Library
   Select Consolidate files & also Reorganise files… if the option is available.

   This will ensure all data is ready to carry to the new machine.

2. Copy your iTunes folder structure in its entirety from C:\Users\[name]\Music\iTunes on the Windows machine to ~/Music/iTunes on the Mac.
   _{~/Music is Mac shorthand for myBootDisk/Users/myName/Music}

   Don't export/import, just copy it all.

   Don't launch iTunes on the Mac yet.

3. Using a text editor - TextWrangler (freeware) is good for this type of task - open the iTunes Music Library.xml file [there may be several copies, with random numbering schemes, but you need the 'simple' one.]

   Don't worry how complex this file looks when you open it, this task is simple
   About 10 lines down you will see a line similar to
   >Music Folder</key><string>file://localhost/C:/Users…. etc… etc

   Drag to select from file all the way to iTunes, so you will have something like file://localhost/C:/Users/[name]/Music/iTunes
   Copy Cmd ⌘ C
   Find Cmd ⌘ F which opens a small find/replace window
   Make sure the cursor is in the top box - Paste Cmd ⌘ V

   Type or paste this into the Replace box, making sure you use the correct name for your Mac boot Partition - by default this is Macintosh%20HD
   Note the %20 instead of the space, all spaces need to be replaced by HTML-style %20
   Also check your user name is correct [short name, like jdoe, not John Doe] file:///Volumes/Macintosh%20HD/Users/jdoe/Music/iTunes

4. Take a deep breath… ;)
   Click Replace All.
   Save Cmd ⌘ S
   Quit TextWrangler.

5. This is the bit the guides don't usually tell you
   Go back to your iTunes folder, find the file called iTunes Library.itl [not .xml, .itl]
   Delete it.

   Launch Terminal [Applications/Utilities]
   copy/paste this touch ~/Music/iTunes/iTunes\ Library.itl & hit Return⏎

   This will create a new, broken, .itl file, which will let iTunes rebuild the Library correctly.

6. Launch iTunes.
   It will notice the .itl file is broken & start to repair it. It will show 'Importing...'
   It may take some time, 10 mins to an hour, depending on how large your Library is. it seems to slow down after about 6000 tunes or so.

Done.

When finished, your Library should be almost entirely intact, including playlists, play counts etc.
It always seems to lose a small amount of album artwork, but this should be easy to get back from File menu > Library > Get Album Artwork