Simple Question on using an iPod nano v iPod

I do not have an iPod, but am considering getting one. I have about a 10 gb library of music and have been using a 256 mb mp3 player for the last couple of years. So my process for getting music has been to pick what 50-60 songs I want to hear and load the songs manually. I realize if I get a 30 gb player, I can load my entire library to the unit and update periodically. My question is how iTunes manages music for mp3 players which are smaller than the library. 50-60 songs is one thing, but how do you manually load say 500 songs (i.e. 2 GB nano).
So I guess what is the most common route you ipod users use? Do I need to start making playlist? I currently do not. Does itunes shuffle these 500 songs when connected? Any insight would be appreciated.
Thanks
Travis

If the iPod is smaller than your library there are a few things you can do. You can choose the update option "Sync Music - Selected playlists". If you do this you can update any of the existing playlists you have leaving some out or create a playlist specifically for your iPod and drag the tracks you want into it. If you tire of the list and want to change it, you just add or remove the songs you don't want The ones you take out out remain in the library to be used again. You can read more about playlists at these links:
iTunes: Creating playlists of your favorite songs
How to create a Smart Playlist with iTunes
Loading songs onto iPod automatically
Another option is to set the iPod to "Manually manage songs and videos" and drag whatever you like to it: Managing content manually on iPod
Another way but one which I think is more difficult to manage is to choose the "Only sync checked items" option in the iPod Summary tab. By un-checking a song in iTunes, it will not be updated to the iPod and if already on the iPod, unchecking the song in iTunes will remove it from the iPod during the next update with iTunes.
For the automatic options iTunes will add what you have chosen to put on. You can create a Smart playlist that picks a random selection if you like and there is also an option to shuffle songs on the iPod.

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