Key Decisions for running iTunes on a Server

There is no single best way to set up or migrate your iTunes library on your server.  This section suggests some key decisions that you should think about about how you should configure iTunes and how your media library will work best with iHomeServerâ„¢. 
This topic gives an overview of these decisions, why they are important and where you can find out further information:
Why is this important?
Recommendation for first time install
iTunes (and iHomeServer) judge the uniqueness of a file based on its full file path. 
Therefore, the file
is considered different to
...even though the physical and UNC conventions actually refer to the same file.
If you refer to the same file in different ways you may get duplicate files if the file is under an iHomeServer Watched Folder
Use UNC naming convention always.  It allows a single way of referring to a media file anywhere on your home network, making sharing files between servers and PCs simpler.
Your iTunes Media Folder is where iTunes will store any media it downloads or synchronises from other devices.  You need to ensure you choose a location with enough space to give you capacity for the future
It is recommended that you do not create an iHomeServer Watch Folder that contains your iTunes Media Folder- otherwise iTunes may get confused and iHomeserver may attempt to re-add media that is already  in your library.
A folder on non-system drive, eg d:\iTunes.
For WHS systems, use the Dashboard to create a new Shared Folder called 'iTunes' and point the iTunes Media Folder to the equivalent UNC name,
eg \\servername\iTunes
You don't have to keep your media under the iTunes media folder.  Instead, you can distribute it across multiple hard drives or servers, or maintain it in your own folder structure.  Alternatively, you can tell iTunes to keep any media that iTunes manages in the iTunes Media Folder.
Additionally, iTunes has a feature that allows media that is added to it to automatically get re-organised and re-named based on its metadata.
It depends on whether the convenience of iTunes managing your media folder library outweighs the disadvantage of not being in direct control of your physical media library.
Many users already have iTunes running on their PC or laptop.  Some users have iTunes already running on their servers.  If you migrate an existing iTunes library (and by this we mean specifically, an existing iTunes library database), you need to ensure the guidelines above have been followed - eg existing media was added using UNC naming conventions.  If not, you need to ensure, if you then set up Watch Folders, that no duplicates will be created.
Create a new library.
It is much cleaner to start with a fresh library configured using the recommendations above.
You can re-add your existing media using an iHomeServer Watch Folder.
You can then merge information from your PC (or other WHS) installation of iTunes including Play counts, ratings and playlists using the Ratings, Play Counts and Playlist Importer window
The next section provides some background on how iTunes manages it media.