iPhone sync to Google contacts - 3 methods and work/home implications

[Before you do this, ready my update!]

Why, among all the OS X blogs I read, have I not come across much discussion of this July 2008 iTunes 7.7 Apple knowledge base article: iTunes: Syncing address book contacts with your Google contacts?

For that matter, why does iTunes OS X have no relevant Help articles on the topic?

Maybe it's because synchronization in OS X/XP/Address Book/Outlook/iTunes/iPhone/MobileMe/Exchange/Google Apps/Yahoo! is just ... you know ... a wee bit complex? Maybe I'm not the only one lost in the mine field?

Well, it's time to explore this particular quadrant. I hope to update this post over the next few days, but here's the first draft.

I have made progress lately with Work/Home integration. I use Google Sync to one way sync work calendar information to a secure calendar outside my family domain. I found traditional "subscription" (.ics) to this calendar failed due to Google Calendar problems, but that I could acquire the data via either iCal CalDAV support or Spanning Sync. The latter seems faster and more reliable and I'm using that.

So what about Gmail contacts?

There are several options:

1. gContacts for iPhone - pulled from the App store but supposedly to relaunch without trademark issues. I have this, I use it for read-only access to my Google Contacts. No search however.
2. Spanning Sync for OS X: This will pull Google Contacts into the OS X Address Book. The problem here is duplicate resolution -- I don't know how it works. Note that OS X Address book has a Merge facility I've never tested.
3. iTunes 7.7+ will supposedly sync Google Calendar contacts to the iPhone directly (not via the Address Book). On XP this will replace your iPhone Address Book, but on OS X it apparently creates a separate "account" so you can sync the iPhone via iTunes and the USB cable to both the OS X Address Book and Google Calendar. Note the iPhone Contacts has a limited search capability.
   

I'm going to try #3 after I back up my OS X Address Book and my Google Contacts. Be warned, however, that the Google Contacts backup is CSV based and does not include relationships to mailing lists. It is impossible, given the format, to completely restore the data should anything go wrong. At best you will restore an approximation to your original Google Contacts.

The interesting possibility is that one could synchronize Outlook work contacts with Google, then sync that to the iPhone via iTunes, and, on OS X iPhones only, have some integration of work and personal Address Books/Contacts.

Did I mention than Synchronization is Hell?

PS. Despite the lack of documentation, the very existence of this option, and it's implementation as a separate 'account', is encouraging. It suggests Apple may eventually support Google Apps synchronization as a (far better) alternative to MobileMe. Maybe.

Update 11/2/08: Ok, didn't work. I've restored my OS X Address Book from backup.
If you active iTunes sync with multiple sources, it combines them ALL into a SINGLE source, which it then broadcasts back to all sources. So my OS X Address Book, iPhone and Google Contacts all had the sum of all addresses -- without much attempt at reconciliation (though OS X Address has an interesting "detect duplicates" function). I left my Gmail contacts as the sum of all sources, it's never been a very controlled data set so this probably won't cause too much harm. I turned of Gmail synchronization. Someday I'll fix things up, but for today the project is on hold.

Update 12/1/08: See the comments for a bad outcome from one experiment. Synchronization is Hell.