I had such a hard time transferring my iPod songs to my computer and
importing them to iTunes, I decided to compile all my research to spare you the headache
Let's start with something relatively simple, though absolutely indispensable: transferring songs
from iPod to PC
If, like me, you
manage your iPod music with iTunes, you should have noticed that transfers with iTunes are, surprisingly, only one-way transfers
After a computer crash and a complete system reinstallation, I ended up with all my music being locked on my iPod and no way to move it back to my PC
I opened iTunes and tried to drag my songs from iPod to the "Library", no chance. Then, I tried to slide my iPod songs to my PC, no better chance
After some search on Google, I landed on several websites pretending their softwares were able to do what I was looking for:
transfer iPod music to PC
So, I tried several of them and one quickly got out of the pack:

I am not an expert, but believe me,
this software is damn good !
In a couple of obvious clicks, I was all set: with all my iPod songs, playlists, videos, artworks copied to my computer and even
back into iTunes as I explain it on another page
Enough talking, let's get started!
First you need to
Download CopyTrans
Depending on the web browser you are using, the installation file should either end up in My Documents ⇒ Downloads or on your Desktop
The icon looks like this

Double-click it and follow the installation steps ( if you have never installed a software before and need help on this with

, their
Installation page will help you )
Once installed, you will see a kind of launcher with other programs from the
CopyTrans Suite that I will discuss on other pages of this website, because literally every of them is worth its weight in gold
Click ⇒
|
|
The program opens and you are ready to rock 'n roll

Check the boxes next to the
iPod songs to transfer to your computer
( you can also hold down the Ctrl or Shift keys to select multiple songs at a time or, even simpler, press Ctrl + A to select all songs )

Next step is either to click "Backup to Folder" if you only want to
copy iPod songs to a place ( folder ) of your computer
or "Backup to iTunes" if you also want them to be
inserted to the iTunes Library, which is discussed on the next page of this website

A last screen before the actual operations start lets you choose advanced transfer settings. If you are as computer illiterate as I am, just stick to the default ones, it worked like a charm for me and just click:

A progress bar shows up with information about ongoing operations and when the copy of your
iPod to PC
is over, a summary shows copy result and possible errors
As I had no errors, I just opened the destination folder I had chosen for my transferred songs with great impatience and... Voilà!
All were there, safe and sound, none missing and ready to be imported to whatever music program you use ( iTunes, Winamp, Songbird, etc. )

Next page describes the parallel operation, including automatic
import iPod songs to iTunes