Selecting playlist to sync

When I tried to sync after adding 6 songs, a pop-up box told me I was trying to sync 361 GB when I only had 3.7 GB of free space. So I deleted some of the playlists to create some room. When I then tried to sync, all 290 some songs were wiped off the ipod so now I have zero songs on the ipod.
When I go back and try and sync now, I getr a pop-up box that tells me that some of the playlists selected for syncing aren't available anymore. Tried looking in itunes help, but it is more like itunes ****, no mention of possible fixes or even how to select which playlists to sync.
Anyone have any help?
Thanks

Thanks for trying to help. I have a 2GB iPod. I just DL 7.3 version of iTunes the other day.
When I have iTunes open, I have (across the top)
"File, edit, controls, view, store, advanced, help"
I do not have the Summary, Music, etc that you mentioned in your last post.
When I click on "Edit", then Preferences, I see a pop up box with the following tabs,
"General, Podcast, Playback, Sharing, iPhone, Apple TV, Store, Advanced, Parental Control"
Which tab would I use to select which playlists to syn and which ones not to sync? Or is that somewhere else?
Thanks again!

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iTunes not syncing selected playlists, choosing songs from all playlists
You have it selected to *sync selected playlists* and those playlists are not syncing to the iPod?
however this seems to be very counter-intuitive behavior for iTunes
It can be kind of confusing.
I suggest it's not a bug in that it is acting as it's supposed to.
The option (Fill free space) could be made clearer. Perhaps if they added "with songs at random from the entire library" or somehow added an option to select what the free space will be filled with.)
1) The fact that iTunes it is not obeying the selected options on the screen
Not supposed to do that.
If the playlists all fit and there is free space, what would iTunes use to fill the free space if it only used selected items?
2) iTunes is allowing users construct an unhonorable set of choices out of four options. If "Selected playlists, artists and genres" is not compatible with "Automatically fill free space," then that option should be grayed out.
It is compatible.
If there is free space after your selections are added, what should iTunes use to fill the free space? It shouldn't fill the free space with stuff already on the iPod.

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I am now running iTunes 9 and I can't seem to figure out how to do this. In the old version you could select to sync checked songs and then go to the iPod and select which playlists you wanted. Now it's either all songs and playlists or select playlists. Is there a way to do what I want?

Sync all songs but select playlists.
If you sync all, you don't select playlists.
Now it's either all songs and playlists or select playlists.
And that's how it has always been.
Is there a way to do what I want?
It's exactly the same as it was.
Select the iPod in iTunes.
Click the Summary tab.
Tick *Sync only checked items*.
Click the Music tab.
Select *Sync music* and select *Selected playlists* then tick the playlists you want.
Note that *Sync only checked items* doe snot mnena you cannot sync selected playlists or everything. It simply means if you have items unchecked and they are included in any playlists, they will not sync.

Selecting playlist to sync

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