Plenty of memory... songs won't fit

Question

When I plug it in, it says I have 460mb left of free space, but it started removing songs for me (i.e., it wants me to think I have more songs on iTunes than will fit on my iPod, but why do I have so much free space left?). If I can't fix that, then is it possible to choose which songs it won't put onto my iPod?

Answer 1

You can either set your iPod to update manually and drag what content you want to it or you can set it to "Sync Music - Selected Playlists" and set up a playlist of what you want to go on. You can get details on manually managing here:
Managing content manually on iPod
iPod 101: Fill 'er Up
If you want to used the selected playlist option, open iTunes and create a playlist to update your iPod from, call it -iPod to make it the first playlist in Sources. You can make this a normal playlist and drag whatever you want to it or you can make it a random Smart playlist. If you are making a smart playlist limit it to just less than the size of your iPod (for example 3700MB for a 4G iPod Nano). Now connect your iPod and when it appears in the Source list click on the iPod icon to bring up the preference tabs in the main pane. Go to the Music tab and choose Sync Music and the Selected playlists radio button. Choose the playlist you just made from the selection and click Apply. You can also sync from any existing playlists by choosing the same setting, you just need to make sure that the size of the playlists don't exceed the capacity of your iPod:
iTunes: Creating playlists of your favorite songs
How to create a Smart Playlist with iTunes
To make a random playlist go to File>New Smart Playlist.
Uncheck "Match the following rule"
Check "Limit to" put "3700" in the number box, choose "MB" from the first list box, choose "Random" from the next list box. Check "Live Updating"
When you want to change the selection in the playlist just delete everything in it and it will add a new selection
You might also want to restore your iPod. Restoring will erase the iPod's hard drive, reload the software and put it back to default settings. Once the restore is complete follow the on screen instructions and it should connect to iTunes and give you a prompt to automatically update your library onto the fresh installation. If you want to update manually or using selected playlists choose no and it will default to manual mode and you can choose whatever setting you like: Restoring iPod to factory settings with iTunes 7