Manual updates are good for when your iPod is smaller than your music collection, or for people who like to custom tweak things. But if your pod is big enough, and you have tons of songs and don’t want a manual “hassle” each time, auto syncing is useful as well. Your choices in this area may change as your music collection grows.
In my iTunes Preferences, Advanced area, I’ve checked the boxes “Keep iTunes Music folder organized” – this works for me. Also I’ve checked “Copy files to iTunes Music folder when adding to library.” This essentially keeps all the music in one place, if you want it there, allowing you do delete anything outside that folder if you don’t need it for other purposes.
That’s under the “General” tab. Go to “Importing.” You can set it to “Import Songs and Eject” which is very handy when you’re importing a bunch of CDs, allowing you to “production line” the process. Also I’ve checked “Create file names with track number.”
I can’t remember having a problem with CD tracks not being found, but occasionally it stops and offers me two choices of albums by the same name and artist. Usually I don’t know which is the right one either, but that’s another story…
I import all my music in the generic MP3 format, and stay away from the Apple’s proprietary AAC, in case my music moves to another system someday. If I were using a Windows system I’d still use MP3 and stay away from other proprietary or rights-managed formats as well.
The same is of course not true for music you purchase online. I’ve bought some stuff from the iTunes Music Store. It’s fine for “normal” use, but if you start copying it around (outside the normal methods) it won’t play. Plus the encoding bitrate is not very high, to keep the downloads manageable. I record my CDs at 192kbps. When I can, I’ll buy CDs and avoid electronic downloads. I have the bandwidth to download actual CD-quality music, but it’s not generally sold that way.
Playlists:
I did one labor-intensive thing to help auto-manage my music. I’ve created Smart Playlists for every artist I have a dozen or more songs for, and one for each letter of the alphabet, for the myriad artists I have only a few songs from. This way, when new stuff comes it it automatically shows up in one of those playlists. If I get too many of a given artist under their letter, I create a new Smart Playlist for that artist.
If you don’t do that, you can’t easily look up artists by name, because they will be listed separately every time they collaborated with someone else, or when John Mellencamp changes his name (again) or when someone misspells it, on those tracks you may have gotten from questionable sources. Beatles will be listed separately from The Beatles as well.
Then I created a big playlist called “All Regular Songs,” which basically includes all my music except some soundtracks (I have them divided between “movie songs” and “movie music”), comedy clips, other spoken-word stuff, and Christmas music. For most of my iPod listening I shuffle my All Regular Songs playlist, so I never know what I’m going to hear next.