Syncing with multi Mac household

Our household has several iOS devices, a soon-to-be-upgraded MacBook and a new Mac Mini Server. Since we're not working with many users (yet), I'd like to get things organized and working before time becomes an issue. The Mini has a local-only account that has the master iPhoto and iTunes libraries (for sharing with Apple TV's, iPhones, iPads, etc) - with iTunes I have a few options:

1. Everyone shares the same iTunes library
2. Master library is shared, users have their own smaller libraries
3. Master library is shared using home sharing, users have their own smaller libraries

The other accounts are networked (with portable home directories). Since mobile accounts will be in the near future, I'd like to avoid number 1 (and I need some sort of sharing to serve to Apple TV's, iPhones, iPads, etc anyway). Number 3 could be an issue since home sharing is limited to 5 devices, and I'd like a solution that could handle around 10. This brings me to three questions:

1. Can home sharing work with iPhones/iPads that are connected through a VPN to the Mini Server?
2. Is there an elegant way to update the master library whenever a user adds content to their own iTunes library?
3. Does anyone with a similar setup have any tips?

I have a similar setup - 5 iPhones, a couple of computers, iPad, etc.

I have the masters on my Pro - it's always on and powerful enough to keep iTunes and iPhoto running in the background.

Each user has their own iCloud account for email, calendars, etc.

We share a single family AppleID for purchases - this is setup on each device for Music, Videos, and AppStore.

Given that all music, videos etc are bought using the same ID, when they're bought on a device they sync into iTunes on the central library Mac automatically. Each device can optionally turn on downloads of purchased items from other devices. That's a per device setting.

Each user controls their own iPhotos - this isn't a problem for the kids. Between my wife and I, put our own photos into our own iPhoto libraries. Both are shared, and we can drag and drop between them as needed within iPhoto. This doesn't sync automatically, but it's easy to tell on the event level what needs updating.

Home Sharing allows all devices to play whatever music and videos within the houses' wifi network, including on the AppleTVs. HomeSharing also (at least used to) allow for automatic syncing between devices to keep everything on one account, if added outside of the store. With laptops for the kids, they can keep their own smaller libraries and stream via HomeSharing in the house, and copy to their own accounts to store stuff for outside the house.

Outside the house because we're using the single account, everyone can play any music via iTunes Match. With the latest Apple update, this now includes movies and TV shows bought through iTMS.

Have you considered iTunes Match for music & iCloud Photo Stream for the photos?

There is a total of 4 people in our family and between us we have 5 iOS devices, an Apple TV, a few laptops and an iMac. The iMac is setup as our main digital hub. It contains our master iTunes and iPhoto libraries. Here is our setup:

Music Setup:

• We have one Apple ID that all iTunes & App Store purchases are made from.

• The iMac contains a local copy of all our music and is set to sync with iTunes Match.

• All other devices* (OS X and iOS) have iTunes Match turned and do not have local copies of the music files (this has cleared up over 40 GBs form my Air!).

• All devices have access to all the songs and can play them either by streaming or by downloading from the cloud and playing them locally.

• Any added music syncs back up with iTunes Match and is available from all devices (this also works for correcting meta tags).

*One exception is our kids' iOS devices, we have iTunes Match turned off on them and sync songs via direct connection to the iMac and manually selecting the songs via a playlist as we don't necessarily want them to be able to listen to all our music. This also makes it simpler for them to find what they want to listen to (they're 6 and 3 years old).

Photo Setup:

• iMac contains our main photo library and has Photo Stream turned on.

• All other devices** (OS X and iOS) have their own photo library and have Photo Stream turned on.

• The iMac automatically downloads all photos taken from all devices with Photo Stream turned on.

• All devices have access to all photos that are in the Photo Stream and can add to their libraries if desired (this can also be an issue, as all will see everyone's photos).

** One exception here is that I use a different iCloud account from the others as I use my devices for work and therefore keep a separate photo library. All my devices sync to my iCloud account. When I do take family photos on my devices I need to manually add them to the family iMac.