Tips & Tricks..Managing songs and playlists - the basics

Firstly, here's a few general points:

In iTunes, if you the click the arrow icon to the left of your iPod you can see all the songs, videos (listed under "movies"), TV Shows, and playlists on your iPod:

You have to select your iPod in the Source list to see the iPod properties:

Then the iPod properties window appears

In iPod properties you can choose to "Manually manage music" or not. Let's consider these two options:

1) Automatically updating all songs and playlists

If you choose NOT to manually manage your music then your iPod is in Automatic Update mode: after you synchronise your iPod with your computer any modifications to tracks and playlists you have made in iTunes will be precisely copied onto your iPod. When in this Automatic Update mode, you cannot change the tracks on your iPod while your iPod is attached - the tracks in the song list when you are looking at the songs on your iPod appear greyed-out:

The idea is that you make your desired changes in iTunes with your iPod disconnected, and then you connect your iPod which will synchronise with iTunes.

See this Apple article on Syncing Music to iPod.

2) Manually manage music

If you select to manually manage your music, any changes you have made to songs and playlists in iTunes will NOT be automatically copied to your iPod. You will have to manually select and drag the songs from your library onto the iPod icon in the source list. For this reason, the tracks in the song list no longer appear greyed-out (you have to be able to select and drag them):