Over the last few weeks my wife and I have come to the realization that knowing each other's schedules would be really helpful and we've started down the path of sharing our calendars.
Me (work): I use Outlook 2003 100%.
Me (personal): I use my Google Apps for Your Domain (GAFYD) calendar.
Wife: Outlook 2007 100%.
One of our primary goals was to try and find a free way to accomplish this task. After some looking around, the consensus is that we will use Google Calendar (GCal) as our go-between. I looked at what Scott Hanselman is doing since I've heard him talk about this on his podcast. He uses SyncMyCal which can probably do everything my wife and I are needing except that it fails the free requirement.
I then looked at Google's Calendar Sync tool but it will only sync up with the primary calendar. That's no good - even if my wife and I shared our GCal's we couldn't sync with each other's and so it didn't seem like that would work either. I threw out a tweet looking for suggestions and I got some great feedback (Twitter is great for things like this).
Prokrammer had the best idea that I thought might work for us and still be free. He recommended that I use the Google Sync tool since it was free, but create a GCal for my wife on my domain and have us both sync with it. Because this new calendar was in my domain I could grant myself full rights to it and could edit as needed. With this setup I would one-way sync my work calendar to it and then my wife would 2-way sync it with her Outlook calendar.
I would be providing my wife with my work calendar and she would be giving me her personal calendar via GCal. I would then use her shared GCal as my primary calendar and will make all of my personal appointments on it. Then, she too would get them when she synced up.
This sounded like it would do the trick...All the planning in the world doesn't take into account software failure. The GCal sync tool, for some reason, can not access my wife's calendar. It gives a beautiful error "Could not connect to Microsoft Outlook: error -2147319779, code 0".
Unless Google provides and update with the fix I guess we will have to bail on the free requirement and purchase something.