Can I Play "Checked " and "Unchecked" Songs on PC Automatically???

Question

I want to Sync only checked songs from my Libray to my Ipod, so I don't use up all it's capacity. But, when I play songs from my PC, only the "checked" songs play automatically. It skips over the "unchecked" songs in any list. Is there a way to fix this so that all my songs on my PC will play together, or do songs need to be checked to play automatically in any list???

Answer 1

*do songs need to be checked to play automatically in any list???*
Yes they do. Using unchecking to manage an iPod is an option (and works fine when you are working with a small number of specialised tracks such as Christmas songs) but only if you can live with the other things unchecking does:
Unchecked songs will be skipped when playing songs from the library or a selection. They will only play when individually clicked on.
Smart Playlists have an option that unchecked songs won't appear.
Unchecked songs will not be burned to CD.
Genius will not use the songs that are unchecked.
Another method you can use to auto-sync your iPod with iTunes is "Sync Music - selected Playlists". Syncing selected playlists is just like syncing your whole library only on a smaller scale and more "selectively". This is particularly useful when your library is larger than the capacity of your iPod. When your iPod is is set to sync selected playlists it automatically picks up any changes you made to that playlist in iTunes since you last connected. Anything you added to the playlist will be added to the iPod, anything you deleted from it will be deleted from the iPod. In other words the iTunes playlist and the iPod are kept "in sync".
Open iTunes and create a playlist to update your iPod from, call it -My iPod for example (the dash will position it at the top of the playlists in Sources). Drag whatever content you want to have into the playlist. 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: Syncing Music to iPod