What is the best way to configure my iPods and user accounts?

I'm looking for a little guidance. Here is my situation:
I am running the latest version of Tiger. It is currently configured with three accounts; mine is the admin. account and each of my two children have their own accounts.
My account is the one that is used most of the time. All of our calendars in iCal are maintained here including one for each of the kids. Each of the kids has their own Contacts list in the Address Book as well. I currently have a 5G 30GB iPod Video that I sync with iTunes through this account. Shortly, I will be buying an iPod Touch. I want my 30 GB iPod to be the one that has everything on it; it will be the one we take in the car on trips for music. I want the Touch to have some, but not necessarily all, of my music and all of our calendars and contact information. I am looking to use it to replace my Palm as my PDA.
My son has a 2G Nano which currently syncs through his account.
My daughter will be getting a 3G Nano soon.
I will also be upgrading to Leopard very soon.
Ultimately, I would like each of the kids to have their own iTunes libraries for music and podcasts and to sync their iCal calendars. As I understand it, however, they cannot access their calendars from their own accounts under my current arrangement. I also understand that there are several ways to configure my Mac to work with multiple iPods.
Given all of this, what is the best thing for me to do? Should I set up all of the kids' iPods to sync through the admin. account so they can get their calendars at the same time? Or is their some way for them to have access to their calendar information from their own accounts under Tiger (or Leopard)? And as far as my two iPods (the Video and the Touch), should they sync through separate libraries, or through one using playlists. I also want to minimize duplicate data wherever possible, be it music or records in iCal and the Address Book.
Thanks in advance for any suggestions or advice!

Anyone...anyone? Bueller...Bueller?

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