Question : Problem: Syncing iTunes library between two computers and one backup server...

Now that we are DRM-Free...

I have my computer and my wife's. I run VISTA, she runs XP.

We have a fileserver running Win2003

I want exact copies of the iTunes library everywhere (on these three machines) and I want it to sync automatically and I want it to show up in the library automatically.

Let me explain...

I buy a song, it downloads to my machine. Automatically it syncs to my fileserver. Automatically it is synced to my wife's computer and automatically when she opens iTunes, the new song is discovered.

If my wife buys a song, I want to see it too, in the same manner.

What is the best solution?

Answer : Problem: Syncing iTunes library between two computers and one backup server...

F both your libraries contain the same music at this present time, I would just dump it up to your server/NAS and then sync it back to the computers.  Test it out with some dummy files... Here is the command I would use

robocopy.exe /S MIR x:\sharedItunesLib "c:\documents and settings\userName\Desktop\testDir" /LOG+:c:\pathToStoreLogFile\file.txt

----------------------------------------------------------------------
ROBOCOPY v 1.96  :  Robust File Copy for Windows NT
----------------------------------------------------------------------

 Started : Wed Jan 07 20:10:21 2009

             Usage : ROBOCOPY source destination [file [file]...] [options]

            source : Source Directory (drive:\path or \\server\share\path).
       destination : Destination Dir  (drive:\path or \\server\share\path).
              file : File(s) to copy  (names/wildcards: default is "*.*").

Copy options:    /S : copy Subdirectories, but not empty ones.
                /E : copy subdirectories, including Empty ones.
            /LEV:n : only copy the top n LEVels of the source directory tree.

                /Z : copy files in restartable mode.

              /SEC : copy SECurity info (both source and dest must be NTFS).
           /SECFIX : FIX SECurity info on existing files and dirs.
           /TIMFIX : FIX TIMestamps on existing destination files.

              /MOV : MOVe files (delete from source after copying).
             /MOVE : MOVE files AND dirs (delete from source after copying).

            /PURGE : delete dest files/dirs that no longer exist in source.
              /MIR : MIRror a directory tree (equivalent to /E plus /PURGE).

  /A+:[R][A][S][H] : add the given Attributes to copied files.
  /A-:[R][A][S][H] : remove the given Attributes from copied files.

           /CREATE : CREATE directory tree structure + zero-length files only.
              /FAT : create destination files using 8.3 FAT file names only.

File Selection:  /A : copy only files with the Archive attribute set
                /M : like /A, but remove Archive attribute from source files.
  /IA:[R][A][S][H] : Include only files with some of the given Attributes set.
  /XA:[R][A][S][H] : eXclude files with any of the given Attributes set.

/XF file [file]... : eXclude Files matching given names/paths/wildcards.
/XD dirs [dirs]... : eXclude Directories matching given names/paths.

   /XC | /XN | /XO : eXclude Changed | Newer | Older files.
         /XX | /XL : eXclude eXtra | Lonely files and dirs.
               /IS : Include Same files.

            /MAX:n : MAXimum file size - exclude files bigger than n bytes.
            /MIN:n : MINimum file size - exclude files smaller than n bytes.

         /MAXAGE:n : MAXimum file AGE - exclude files older than n days/date.
         /MINAGE:n : MINimum file AGE - exclude files newer than n days/date.
                     (If n < 1900 then n = n days, else n = YYYYMMDD date).

Retry Options: /R:n : number of Retries on failed copies: default is 1 million.
              /W:n : Wait time between retries: default is 30 seconds.

              /REG : Save /R:n and /W:n in the Registry as default settings.

              /TBD : wait for sharenames To Be Defined (retry error 67).

Logging Options: /L : List only - don't copy, timestamp or delete any files.
                /X : report all eXtra files, not just those selected.
                /V : produce Verbose output, showing skipped files.

               /NP : No Progress - don't display % copied.
              /ETA : show Estimated Time of Arrival of copied files.

         /LOG:file : output status to LOG file (overwrite existing log).
        /LOG+:file : output status to LOG file (append to existing log).


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