While there are a number of options to get purchased music off the iPod, Apple offers absolutely no official way of retrieving songs you've ripped yourself.
However, luckily, there are 3rd party utilities that can copy music directly off an iPod.
SharePod may be the easiest utility for you: http://www.getsharepod.com/
Download and install SharePod on the computer.
Once you have the above installed, connect your iPod to the computer. If iTunes starts, quit it.
They actually have a fairly decent set of instructions at the following link. http://www.getsharepod.com/help/how-to-transfer-music-from-iphone/
Once you are finished copying them from the device, quit SharePod and then disconnect your iPod from the computer.
Start iTunes and verify all music is there.
Find a song that was imported from the iPod and make sure you can play it.
If it looks complete, you should be all set!If you still have concerns, please do not negatively rate my answer, simply reply back before rating. I'll be more than happy to work with you further
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