Attempting family organization.

I’ve had a family project in the back of my head for a year or so, but I’m finally just getting around to seriously doing something about it.

I’m trying to create a group calendar for Robin and I (and I suppose, for other members of our family if they’d like) so that we can keep track of not only birthdays and anniversaries, but also who has what going on during the week so we know when we have to drive separately to work, etc.

Using Google Calendar as the group calendar application seems to be the easy and obvious choice. The trick is getting that calendar properly synced over the air to our devices.

For Robin, we have a Palm Centro. For me, we have a company-issued BlackBerry Pearl and an iPod touch with the 2.0 software upgrade.

At this point, we’re still pretty straightforward. I read that GooSync is a great application to sync Robin’s Centro to the Google Calendar. Not too happy about the fairly expensive (a little over $39.00) yearly subscription model, though.

On my side is where it gets a little bit tricky. Right now, I’ve got my Exchange calendar syncing via Entourage 2004 to iCal using Sync Services. From there, iCal syncs with Plaxo which ultimately syncs to Google Calendar.

There’s a couple problems with that. First, even though it works, it’s certainly a lot of steps and therefore potentially a lot of points of failure. I looked at taking Plaxo out of the equation and replacing it with Spanning Sync but again, there’s that pesky $25.00 subscription model, and a $65.00 one-time price seems a little pricey for such a utility.

The biggest problem is this… By using Sync Services to keep my Entourage/Exchange calendar synced with Google, instead of breaking my Entourage categories into separate iCal calendars, it dumps all my events into one Entourage calendar in iCal. This is not an acceptable solution because our daily business meetings will get co-mingled on one calendar. All we need to share is family-related events.

I just started looking at taking the desktop out the equation altogether and using Google Calendar sync software on my Blackberry. If this application will allow me to synchronize only certain categories over to Google Calendar then we’re golden. The absolute last thing I want is to lose the data in my Exchange calendar. I would be so hosed it’s not even funny.

Otherwise, this whole thing is just a huge cluster. You’d think that my idea would be fairly common and that a rather obvious overall solution would exist. Have you taken the plunge and set up a group calendar for your family? How did you get it to work? I’d love to know if there are alternatives out there that I haven’t considered. Remember, the variables to this are:

• Google Calendar
• Palm Centro
• BlackBerry Pearl
• Mac OS X/Entourage/iCal
• solution MUST work over the air and not require USB synchronization