Syncing/Updating iPod Question

I have about 990 tunes on my iTunes that are all added to my iPod. If I want to add say 5 songs to my iTunes and I click on "Update iPod" will it update all 995 tunes now or will it recognize that the only tunes not on my iPod on the 5 new songs I just added to my iTunes library?
Am I better off doing a manual update and manually adding the 5 tunes to my iPod?
The reason I ask is because recently I just had all my songs on the iPod and not in iTunes. When I did this whenever I added tunes to the iPod the songs would not show up alphabetically making it difficult to search for a specific song. Someone told me that you could correct this by managing your songs in iTunes and then updating your iPod. I just don't want it to update all 990 tunes every time I update my iPod. Just the new ones and any playlists that have changed.
Thanks.

when you synch automatically only the changes get synched - that includes any changes to teh info in the Tag, playcounts, artwork added etc.
The basic answer in to your question is yet it will only add the 5 songs you added in iTunes.
BUT as you have found out if you delete songs from iTunes and are on auto synch they will delete from teh iPOd next time you synch

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