Sync says complete but doesn't copy anything

Question

I have more music than space on my iPod nano so I've been using the "Sync only ticked songs and videos" option. But when I add new music to iTunes in tries to sync every time I open iTunes and if there isn't enough space it just tries to copy what it can, which is a pain. I've selected "Prevent iPods and iPhones syncing automatically" under Devices in Preferences but that doesn't seem to do anything.
I read that selecting "Manually manage music and videos" would stop it syncing automatically so I selected this. But this disables "Sync only ticked songs and videos" and I'm assuming the only way to get songs on my iPod is by dragging and dropping, which isn't really very practical when you've got nearly 5,000 of them. So I deselected "Manually manage...".
At some point, everything on my iPod got wiped. I've tried syncing and it says it's completed but there's still nothing on the iPod. I thought it might be because "Enable disk use" got automatically selected when I selected "Manually manage..." but turning this off doesn't help. I click Sync and straight away it tells me it's synced but still no music on the iPod.
Sorry for the essay, but thought I should give as much info as possible. I'd be really grateful if anyone could tell me how to fix this.
Thanks... Wilona

Answer 1

Hi, welcome to Apple Discussions.
Glad you got sorted, but it might be worth clarifying a few things.
*Prevent iPods and iPhones syncing automatically* changes the behaviour when you connect your iPod if it is also set to sync automatically. When this option is checked you have an opportunity to change your selections before clicking a button to begin syncing. If this option is unchecked and your iPod is set up to sync then it will do so as soon as you connect it. In manually manage mode this option has no effect.
If your device is smaller than your library and you've not opted to sync with selected playlists then it will fill up with the oldest checked entries in your library and then stop. Subsequent sync operations will be unable to add any more data.
When you switch to manual manage from automatic all the content currently on the iPod will remain until you actively delete some of it to make room for something else.
You don't have to work with single files when dragging & dropping or selecting items to delete. You can use SHIFT & CTRL to specify ranges and add or remove individual items from the range. With the browser active you can also drag albums, artists, genres etc.
A good way to get started would be to create a smart playlist, called soemthing like "Sync List" or "My Tunes", with the rules *Playlist is Music* and *Limit to X Gb selected by most recently added*. Where X is a bit less than the capacity of your iPod. Then set your iPod to sync with that. This will ensure your most recent additions get included. You can improve things by creating regular playlists called "Essentials" and "Exclude". Modify the first playlist so that it becomes *Playlist is Music AND Playlist is not Exclude, Limit to...* and sync both this and the "Essentials" playlist to your iPod.
tt2