How to transfer files from an iPod to another one using iPod 2
iPod
First, you will need to
download iPod 2 iPod
from here.
1- Although iPod 2 iPod will detect and automatically close
iTunes... We do not recommend attempting to run iPod 2 iPod while iTunes is
running.

2- When iPod 2 iPod first starts it appears as follows:

Connect your first iPod device via either USB/Firewire
connectors.
It will take iPod 2 iPod approximately 15 seconds to auto
detect then display the music from your first iPod.
Your first iPod is identified as a 'tab' on both the left and
right sides of the screen.

3- Transferring music
Select
the songs you wish to transfer and either drag them to the destination panel, or
click on the "arrows" to transfer music from one iPod to another.
4- iPod 2 iPod is a simple application to use. All
functionality is driven via the ‘Graphical icons’ on the main menu bar or from
the ‘Right Click’ menus initiated within the song list.
Graphical icons

As the default iPod 2 iPod displays all songs on your iPod.
Use "Playlists" to manage the playlists on your iPod.
While iPod 2 iPod automatically creates a "Backup" of each iPod when it is first
connected. You may use this function to make subsequent backups.
"Restore" allows you to easily restore from a previous backup. Simply click the
"Restore" icon and iPod 2 iPod will automatically restore your iPod to the same
state as your last backup.
The "Advanced Filter" is particularly useful for the viewing and management of
large music collections.
The "Eject" button will detach the currently selected iPod. It is important that
you only disconnect using the eject buttons; simply disconnecting at either end
of your cables could cause damage to your system and/or iPods.
The Right Click Menu
Use the "Right Click" menu to carry out a range of actions on
the individual song tracks.
To initiate this menu place the cursor over the music list
and click on your right mouse button.

Play: Enables you to listen to the currently selected
track.
Show All: Shows all music on your iPod. Useful when
viewing songs within playlists.
Select All Songs: Selects all music within the song
list.
Select Similar Songs: Selects all songs matching the
text in the first column.
Find Duplicate Songs: Finds duplicate music on your
iPod. You will be given the option to clean-up any songs found, freeing up
space!
Find Unlinked Songs: An annoying issue in iTunes, the
"Unlinked Songs" function helps discover music titles which are no longer
associated with the actual music file.
Find Unique Songs: Compares the iPods in the left and
right panels, and displays the songs which are on one iPod, but not the other!
Delete Selection Removes music no longer required.