Unless your iPod/iPad/iPhone easily holds all the music in your library, or you want iTunes to decide what you carry around with you, you'll want to be selective about what you load onto your iPod. There's a relatively easy way to do this, and then you can use all that saved time to laugh at everyone who insisted on a player that gets fed by dragging and dropping files.
So first, the basics: iTunes keeps track of what you want to copy from your local iTunes library onto your iPod/iPad/iPhone etc. Plug your iPod in and a new set of management screens appears, split into sections for music, movies, apps etc. Each time you connect and do a "sync", stuff is added to or removed from your iPod according to what you told iTunes to copy onto it (a separate set for each device, if you have say an iPhone and an iPad). You can go in and tell iTunes to sync selected playlists, albums, artists, genres etc.
The problem with using this screen to manage your iPod is that it's a pain to constantly toggle individual albums or tracks on or off. And you can only get to this screen while your iPod is connected. Thankfully, there is a way to basically avoid this screen, and easily manage what's on your device without actually needing to physically plug it in (and yes, a new release of iOS may ultimately remove the need to plug your iPod in). If you are already managing your iPod this way (and I did see a mate managing music on his iPhone like this and it was horrifically unsustainable) then fear not. Just go to the music sync menu and un-tick everything until there's zero music selected (just watch the capacity bar down the bottom of the iTunes screen). Killed all your music? Good, now we can start.
First, create a playlist called something like "on my ipod". If you own multiple iPods/iPhones etc, you may need a playlist for each device. Now go to library->music and select items from your main library, drag-and-drop them onto this playlist. Select the playlist and start browsing the stuff on (or destined for) your iPod. This playlist is probably going to get quite big, so I'd go turn on the column browser and then you can use the playlist like a "mini library" of the stuff on your iPod.
If you're like me and juggle selections from 60GB of library onto a 32GB iPod, you'll want to delete stuff so you can add new purchases, so just go to the "on iPod" playlist and delete tracks, albums, whole artists. Note this doesn't delete the music, just removes it from the playlist. And as the only unit of iTunes music currency is a "track", you can delete chunks of an album (eg. the bonus live/demo tracks) from the portable playlist to save space.
OK, this solution doesn't solve all your problems - specifically, if you build and use a lot of playlists, you could be back to manual management, because you'll have to tell iTunes to sync several (or all) playlists, and the more playlists you have, the more likely that there are songs that aren't on your big "on iPod" playlist, and it becomes a less and less-accurate guide of what's likely to get copied. Don't have a solution for this yet, I'm mostly an "entire albums" guy, so I don't have much use for playlists anyway.
You will need to watch the size of such a playlist (go to your "on iPod" playlist, select "all artists, all albums" from the column browser and check filesize at the bottom of the iTunes window), and keep this a little under the supposedly available free space - annoyingly, iTunes won't warn you. If you find that some recently added tracks (usually the first track of an album) are missing, you've run out of space. The good thing is, managing what's on your iPod this way is easy - just remove something you're unlikely to want to listen to from the playlist (that's deleting tracks from the playlist, not the library) and re-sync.
Ultimately this "on iPod" playlist is just a playlist like any other, we're just cheating and using it as a way of managing a second library of songs. In the synchronise options, set to only synchronise the iPod with this one playlist. The changes get replicated when you plug-in your iPod. You are now using iTunes to easily manage what's on your iPod.
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