> Apologies for repeating several often-asked questions about iTunes and
> iPod here, but I'm about to do a major reorganization of audio files for
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>
> * Uncheck "Keep iTunes Music folder organized" -- right?
Irrelevant if you have configured iTunes to not copy files to its music
folder, and the only music added to iTunes is dragged into it from
elsehwere on your hard drive. This setting only affects the iTunes Music
folder, and you won't be using that folder.
> * Also uncheck "Copy files to iTunes Music folder when
> adding to library" -- right?
Yes. This is the only critical setting. With this option unchecked,
iTunes won't copy any files you drag into it - it just keeps a reference
to the files within its database.
iTunes _will_ modify your original files, specifically to update ID3
tags as you make changes to metadata in iTunes. As far as I know it
won't rename the files or move them.
> * Uncheck "Create file names with track number" -- right?
> (I don't want iTunes creating or messing with my file
> names -- the files already have the names I want)
Also irrelevant. This will only matter if you use iTunes to rip music
from CDs, download songs from the iTunes store (maybe), or have
configured iTunes to copy files to its music folder.
> * Finally, what do I enter for "iTunes Music folder location"?
Doesn't matter. Leave it where God intended it to be (in Music, in your
home folder). It will be empty. The iTunes Music folder will only be
significant if you use iTunes to rip music from CDs, download songs from
the iTunes store, or have configured iTunes to copy files to its music
folder.
> (I'd like to have different files live in different folders all over
> my HD -- though I could live with all my folders being inside
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> Anything else I need to do before I start dragging groups of these files
> into a virgin iTunes Music Library?
If your original files don't have useful data in their ID3 tags, then
you should address this first. iTunes is entirely based around ID3 tags.
Folder structure and filenames are ignored.
iTunes wants to organise its library by Genre (optional), Artist, Album,
Track number and Title. If these ID3 tags are missing or don't contain
consistent data you will end up with a complete mess. I've seen cases
where hundreds of tracks are called "Track 1" (or similar) with no other
information. Not at all useful.
You can also create playlists and smart playlists which organise things
any way you like, but if your ID3 tags are no good then you won't have
anything to work with.
You can of course use iTunes to enter this data afterwards but it would
be better to fill in at least Artist, Title and Album (and preferably
track number, if you care about album structure) before the songs hit
iTunes. You could use iTunes to assist if you add tracks in small enough
groups (e.g. one album at a time), as you can shift-click a range of
tracks and get info to change details for several at once. I believe
there are also tools for doing things like copying filenames into track
titles. Check out http://dougscripts.com for some useful iTunes
automation scripts.
> And then, after I've set the above preferences and start loading my file
> into iTunes, since these files exist in small organized groups on the HD:
>
> * Can I actually drag each such group *as a group* from its HD
> location into its own iTunes playlist, right from the start?
No. You have to drag them into the iTunes "Music" library before you can
organise them as a playlist. You could set up a smart playlist which
tracks your most recent imports, and then create a normal playlist from
that.
> * Can I simply drag a group's enclosing folder into iTunes,
> or into a playlist?
If you drag a folder into iTunes (specifically into the "Music" library)
it will scan the entire set of subfolders and add all the music files to
the library. (You can't go directly to a playlist - see above.)
> * Can I drag *nested* folders, each containing some "songs",
> into iTunes?
Yes, as above.
> Finally, if I manage to get all my audio files into iTunes in this way
> --- which I think will really mean that they've all been **cataloged**
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> as if they were in the iTunes Music folder? (which, I realize,
> is where God, and Steve Jobs, intended them to be)
Yes.
> * Will I be able to modify metadata like Genre and Album for
> these files using iTunes, just as if they really were in the
> iTunes Music folder?
Yes. This stuff is mostly stored in ID3 tags inside the individual files
(with a cached copy in the iTunes library database files). Some data is
in the iTunes library only (e.g. "last played").
> * Will I be able to modify individual *file names* in iTunes, and
> have the original files be re-named, as seen in the Finder?
No. iTunes doesn't provide any way to change the filenames (unless you
have the files in the iTunes Music folder and have the appropriate "keep
organised" features turned on, in which case iTunes manages the
filenames automatically). It does show them in the Info window.
> * And should I stick to strictly manual synching, so that
> iTunes doesn't try to undo everything the first time I
> reconnect the iPod after its been loaded the first time.
Um, not sure what you are asking there. The iPod is a separate issue,
and it receives data from iTunes (it doesn't cause modifications to the
iTunes library, except for some data like "last played" and the play
count).
If you have the iPod configured for automatic synching, then it is
"owned" by a specific copy of iTunes and every time you connect it,
iTunes will automatically update the iPod for appropriate changes in the
library, by deleting, adding and replacing songs on the iPod.
You can set the iPod to automatically sync with the entire library or
just selected playlists.
If you have the iPod configured for manual synching, then you have to
manually add, remove and modify items on the iPod, and can do so from
any computer running iTunes (constrained by host platform - if the iPod
is Mac-formatted then you can't manage it on Windows, but if it is
Windows-formatted then you can manage it on both Mac and Windows).
If you change between manual and automatic modes (or vice versa), iTunes
will want to wipe the iPod and start fresh.
> And I guess I won't even ask what will happen to the iTunes links if I
> move one of these files elsewhere using the Finder, or rename it in the
> Finder . . .
I suggest a controlled experiment.
In general I'd expect iTunes on a Mac to be quite happy if you make
folder-level or file-level changes within a volume (as long as you don't
try to move files to a different drive or partition).
For example, you should be able to rename folders and move them around
without causing problems. (This is the magic of HFS+ aliases.) Moving
files to different folders will probably be OK, as will renaming files.
If you renamed or deleted a file then put another one in its place with
the original name it might confuse things.
> Thanks much for any advice or assistance (and this is on a MacBook
> running 10.4.11, currently using iTunes 7.6.2, and intended for a black
> 8 GB iPod purchased late last year).

Signature
David Empson
dempson@actrix.gen.nz
sbt - 12 May 2008 14:48 GMT
> > And then, after I've set the above preferences and start loading my file
> > into iTunes, since these files exist in small organized groups on the HD:
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> it will scan the entire set of subfolders and add all the music files to
> the library. (You can't go directly to a playlist - see above.)
Sorry, but the above is not completely accurate. You can drag a folder
of songs to the "PLAYLIST" header in iTunes sidebar and it will create
a playlist of that name containing the songs in that folder. It will
NOT create a nested folder structure, though, just a flattened playlist
with all the contained songs.

Signature
Spenser
David Empson - 13 May 2008 10:44 GMT
> > > And then, after I've set the above preferences and start loading my file
> > > into iTunes, since these files exist in small organized groups on the HD:
[quoted text clipped - 19 lines]
> NOT create a nested folder structure, though, just a flattened playlist
> with all the contained songs.
Thanks for the correction. That was a feature I didn't know about.
You can also drag a folder directly to an existing playlist and it will
add all the songs in the (nested) folder hierarchy to the library (if
necessary) and to that playlist.

Signature
David Empson
dempson@actrix.gen.nz
David Empson - 13 May 2008 10:47 GMT
> > > If you drag a folder into iTunes (specifically into the "Music" library)
> > > it will scan the entire set of subfolders and add all the music files to
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> add all the songs in the (nested) folder hierarchy to the library (if
> necessary) and to that playlist.
I should proofread before I post. By "nested" I mean it will find all
songs in the folder hierarchy. The hierarchy is not replicated in
iTunes.

Signature
David Empson
dempson@actrix.gen.nz