Ideas for managing HD space w/ iTunes / iPod?

Of course you can. But you need to set the iPod to update manually, so that when you connect it to the computer it doesn't update itself automatically. When you set the iPod to update manually you can delete all the songs you want from the HD and still keep them on the iPod, but to add songs to it you'll need to drag them from the itunes library to your iPod, all this through iTunes.

In order to do this, don't delete any of the songs from the HD yet. First connect the iPod and in iTunes will appear a summary of your iPod (This is if you have iTunes 7). At the bottom of the page you'll see a few boxes with some text by the side. Uncheck the one that says 'Update only check items' and check the one that says 'Manually manage music'. That'll do it. Now you can delete all the songs you want from your HD and they will still be on your iPod.

Hope this helps and good luck.

P.S.: when you do this it might delete all the songs from the iPod, after you set it up to update manually, select all the songs in your iTunes library and drag them into the iPod through iTunes. After the process is finish, you can delete all the songs from the HD.

Buy a back-up hard drive and back up all your files on it. That is something that should be done no matter what type of memory you have. I just recently had been lazy on backing up my files and lost 20gb of iTunes. The problem with deleting the songs and then adding more to your iPod is if they are not on your iTunes list you lose them from the iPod when you go to add new ones. If you have a home PC I suggest using that as your main computer for your iPod and iTunes.

try going to my music, right clicking the folder and selecting properties. when the dialog box pops up, click advanced and in the lower portion check the box for "compress contents to save disk space"

If you want 20GB free space take a look here:

https://copy.com/?r=eyfo7S