How to automatically sync itunes to an external portable drive?

Hello,
I've got my library on an external HD connected to my mac mini. here is what I want to do.
1. On connecting a 2nd portable HD to my mac mini
- I want to be able to automatically sync up itunes music/playlists etc.
2. I want to be able to unplug this portable HD from home, bring it work and connect it to windows machine at work and be able to listen to the same music.
Can this be done? I'm a novice, but been told that this can be done wiht the "automator" application?
Any help would be appreciated
thanks,
karthik

As I've replied to your other threads...
Easy method 1:
Move or Copy entire working library from current location to the root of your external drive. Press & hold down shift (option on a Mac) as you click the icon to start iTunes. Click Choose when prompted, then browse to ..\iTunes\iTunes Library.itl on the external. If you copied the library across then test your new library works properly after renaming the original folder, before deleting the original folder to recover space.
Easy method 2:
If you haven't really started to build your library. Press & hold down shift as you click the icon to start iTunes. Click Create. Browse to the root of the external drive. Create the library as ITunes. Drag your media into ..\iTunes\iTunes Media\Automatically Add to iTunes.
Complex method:
Required if you've already tried other things and now have media & library scattered around. See the post make a split library portable.
in addition...
In all cases the idea is to get a library folder called iTunes containing a media folder called iTunes Media with all media inside this media folder. Once you have the library in this shape it is easy to reconnect to the library with the shift-start-iTunes method if the drive letter changes, move the library to another computer, and backup the library by cloning the folder to another drive.
tt2

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