Multiple family mbrs, multiple ipods, multiple accnts, multiple computers

I have a family of 6, we each have various ipods (iphone, ipod, nano, shuffle, etc), and we have multiple computers -- some Mac and some PC.
We need to understand what factors impact the ability to put a particular track on one or more devices, manage a given device from one or more accounts on one or more computers, and share, as allowed, between devices, people, iTunes libraries, iTunes store accounts, for both purchaed tracks and MP3 files that we might already own, etc...
I'm looking for a simple and concise description of all of the factors. Any pointers?
If the iTunes world were simple we could simply each have our own music -- stored in one or more places in one or more accounts, on one or more computers. We would be able to share what we like, and put whatever subset we like on whichever device, manage any device from any account on any computer, etc... Of course this could be subject to licenses, but it should at least be possible to get a statement of what license restrictions exist.
Can anyone suggest any references for this? I assumed it was simple, but anyone who has recently plugged a "guest" iPod into another computer will know this is not the case after having been rewarded with the choice of wiping all content off of the iPod, or somehow transferring the content to the friend / family member (with no clear indication of whether this also comprises transferring the content away from the original user, nor how, if possible, to undo such a move later, etc...)
I have seen an article relating to using multiple ipods with one computer, but it does not address all of the issues -- for example using one ipod with multiple computers, etc...
Thanks in advance.

Let's see if we summarise the main points that will help you decide on a strategy:
+ An iPod can automatically sync (one-way transfer from iTunes to iPod) with just one iTunes library.
+ An iPod (but not an iPhone) in manual mode can accept tracks from multiple libraries.
+ iTunes can transfer (copy) purchases from an iPod into the library if authorised for the account used to purchase them.
+ Networks, memory sticks, portable hard drives, CD-R, DVD-D and iPod to PC transfer programs can be used to move other content between your libraries.
+ The new "home sharing" feature probably has some relevance too, but I've not explored just what the capabilities are.
+ For each account, DRM puchases can be authorised on up to 5 computers at any one time.
+ For each computer, up to 5 accounts may be authorised on it at any one time.
+ Each iPod may hold DRM content from up to 5 different accounts.
+ DRM content may be transfered to as many iPod's as you wish.
+ Most iTunes Store content is no longer subject to DRM, the main exceptions being Movies & Games/Applications.
+ iPods can be formated for use with either Mac or Windows. You can manage content on a Windows formatted iPod with either system, but the reverse is not the case. Firmware updates & restores must take place on the native system.
+ An undocumented/unsupported feature is that if you clone a library (make a complete copy of the iTunes library files and media content) and place this on another machine, an iPod "synced" to the original library will also see any clone as its "home" library. Once cloned you don't have to keep all the content available in each locataion. For regular iPods if syncable content cannot be found corresponding files on the device will be left alone (not updated or deleted).
+ The main database file of an iTunes library can only be opened by one process - multiple users on the same computer or over a network will lead to problems. Always close iTunes before switching profiles.
+ The media content folders can be simultaneously accessed by multiple accounts.
+ Automatic syncing has a number of advantages. You can update tag info. in iTunes knowing that when updated the iPod will recieve all the updates. Using playlists you can manage the content that will go on an iPod without having it connected. Ratings & playcounts can sync in both directions. All the content required to restore your iPod is in one location.
+ Manual management allows you to add content from whichever library you are connected to.
+ iTunes does not keep track of files moved or updated by other programs or instances of iTunes. If you share content folders then it is best to avoid the *Keep iTunes Media folder organised* option. When you update content on one machine, e.g. change a capitalisation or correct a spelling, other libraries will only notice the change if they access the file in some way, e.g. by playing it.
I'm sure there's more that I can't think of just now but that's a start.
*Personal Case history:*
Our family has an iPhone, a Nano, 3 Classics (old & new) and a 5th gen. I started by making most of the purchases on my account, putting the children's gift cards onto my store account for example, but two now have their own accounts. I manage most of the music in one main library that sits on a network. One child has a separate library which started as clone of the original and then had content that he dislikes removed... This means I can update his iPod at either his machine or mine although if I add any of his music I have to remember to update both libraries. When he uses iTunes on his computer he only sees the rock/blues/metal that he likes whereas the main library has everybodys content lumped together.
All the iPods are set to sync automatically using the method two (Sync with selected playlists) from the Apple support document How to use multiple iPods with one computer, although I have a slight twist. Rather than regular playlists I set the grouping field to indicate which users should receive which tracks and create smart playlists based on the content of this field.
e.g.
"Alice's Tracks" is "Playlist is Music" + "Grouping contains Alice" + "Kind contains audio"
"Bob's Videos" is "Playlist is Music" + "Grouping contains Bob" + "Kind does not contain audio"
Tracks that both Alice & Bob want on their iPods have the grouping set to "Alice/Bob"
etc.
This way each of us gets a different selection of content to suit our tastes and the capacity of our iPods. An advantage of using the grouping field is that it is stored in file tags (for non-wav audio files anyway) so that it is relatively easy to recreate the playlists should the iTunes library get trashed. Also useful if you move files about manually as playlist membership is preserved when you delete & re-import the tracks.
However you choose to do things you should also create a backup. My main library gets synced to a portable hard drive using SyncToy 2.1 (Windows) which I sometimes take to work and sync there, giving me three complete copies of my library at any one time and I can update any iPod from any instance of the library. An occasional scan of the contnet folders with iTunes Folder Watch helps me catch up if, for example, a podcast has download at one location but the library is overwritten with a newer version from the other.
Hope that's given you some useful food for thought...
tt2

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