By jove, it works.
Emily and I see each other's calendars, and add items from phones or browser (though for now I don't fully sync my calendar until I sync to my iMac). It's really helping us coordinate family activities, and get more out of the time we have.
That's a win worth the pain I've gone through putting this together.
But what about the next step -- work/home calendar integration? Surprisingly, the cc myself from Outlook/work trick works much better than I'd imagined -- Gmail and gCal are very good at handling these Exchange generated transactions. I'd still like to be able to carry my work calendar around on my iPhone though -- rather than continue using my old Palm.
It turns out there's exactly one way to get work/home calendars on the iphone, but it comes at a significant price, and it's evolved with a major surprise "feature":
So there's a solution, but for now it's strictly an Apple/Microsoft solution. You pay or you don't play, and you do it their way. There are a number of interesting features to this solution:I wrote a few weeks ago that the iPhone was unlikely to support work/home calendar integration. I previously wrote that you can't sync via the USB cable to two different machines.
[I was] Wrong on both counts...
... David Pogue's iPhone Tips and Tricks tells us that Apple has a supported framework for work/home synchronization and an approved method for synchronizing at multiple machines....... To get work/home integration you must abandon the old world of physical connections for calendar and contacts synchronization. Yes, Apple has a vision, and it doesn't involve the USB cable.
The iPhone has a concept of wireless calendar (and contact) providers. So you can have one provider that's MobileMe (personal data) and one that's Exchange server. Both can coexist....
- No cables. Apple would like to reserve the physical cable strictly for transfer of DRMd media - and probably they want to get rid of it all together. Steve Jobs doesn't run everything at Apple, but his dislike of cables is legendary. The future doesn't involve a cable.
- It's very much sync to the Cloud, where the Cloud belongs to Apple. Apple isn't ready to cede the Cloud to Google.
- The approach seems like it might be extensible to multiple providers, but currently there's one conduit for MobileMe transactions and one for the Exchange ActiveSync wireless transaction .
So if you want to go the whole way to work/home integration, you go with Apple, not Google.  MobileMe family account, iPhones for everyone (BB can't sync to MobileMe), and Exchange server at work.
For now it's a bit academic. I don't think I can get my employer to support my iPhone with our Exchange server, MobileMe isn't ready for prime time (no publish/subscribe), and I'm not going to buy another iPhone yet .
Still, it's a sign of hope, albeit one darkened by worries about Apple's trustworthiness.
Oh, what's that? What did I mean by "Surprise Feature"?
Well, that's the entire crux of the matter.
Corporations hate the idea of employees running around with corporate contacts and calendars on an iPhone. They'd really like to keep your contact list sewn up -- one more thing to lose if you switch work. They also hate for those meetings discussion upcoming acquisitions to be lost with an iPhone (the FTC doesn't like that either).
The "Surprise Feature" is that ActiveSync supports a self-destruct signal. The Exchange server can send a "wipe all data" message to the iPhone. This is the key feature that allows corporations to live with the idea of corporate data sitting on an employees iPhone.
It's a good compromise. It means that we might get full work/home calendar, contact, task integration sometime in the next decade, even if we have to sell our first born daughters to Apple.
 Which apparently has nothing to do with the Pocket PC Active Sync that so many people learned to hate. What's with Microsoft marketing? They used to be good at this stuff.
 So will Apple let Google put a sync solution on the phone the way they did for the Blackberry? Based on Apple's recent behavior, the answer may be no -- and so Google might not even try. I'm going to wait on moving Emily to an iPhone until we see how Apple plays this one.