Laptop crashed and how to transfer music from ipod back to laptop and won't transfer new purchases to ipod?

Question

My laptop crashed about 2 days ago. I got it fixed and had to reinstall it. I had to reinstall itunes all over again. How do I transfer all my songs from my ipod including the ones that were from hardcopies and by hardcopies I mean cds I bought in real life and is on a disc. All of the songs are still on my ipod so how do I upload all of the songs and videos (purchases, music/songs from hardcopies/cds uploaded not bought from itunes, etc...?) How would I upload all of that back to itunes on my laptop? Another question is for some reason when I hook up my ipod to my laptop, I recently bought 23 songs about a day ago and it won't upload those purchases to my ipod, is it because I have all the hardcopies and downloads on my ipod that the itunes library doesnt have? Also, how would I sync my newest purchases to my ipod efficiently without deleting any of the hardcopies I uploaded before my laptop crashed?

Answer 1

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If you are using iTunes version 7 or later, then you can transfer purchased iTunes store music from the iPod to an authorized computer by using the "file/transfer purchases from iPod" menu. Note that the maximum of 5 authorized computers applies here.
For all other non purchased music (your own CDs etc) try this method which works on some Windows PCs.
Enable your iPod for disk use.
See: iPod Disk Use.
Open iTunes and select edit/preferences/advanced/general. Put a check mark in the box marked "copy files to iTunes music folder when adding to library" and also "keep iTunes music folder organized", then click 'ok'.
Connect the iPod whilst holding down the shift/ctrl keys to prevent any auto sync, and if you see the dialogue window asking if you want to sync to this itunes library, click 'no'.
Then go to file/add folder, open 'my computer', select your iPod and click 'ok'.
The music files should transfer to your iTunes.
If this doesn't work (and it may not because officially it's not supposed to), check out the instructions/suggestions here.
Music from iPod to computer (using option 2). This a manual method using "hidden folders" and although it works, it can be messy.
Much easier ways are to use one of the many 3rd party programs that copy music from the iPod to the computer.
One of the most recommended is Yamipod. This is a free program that transfers music from iPod back to the computer. However, it does not transfer playcounts/ratings etc.
Another free program is Pod Player.