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End User 

If you want to practice swearing for an hour, try getting your contacts from your Gmail to your Yahoo! address books. Then try migrating your calendar.

It’s doable if you, the trained Googling bear, want to Google through a few hoops to get it done. None of the hoops are on fire, but you might still feel burned on your beary behind.

Wait, now comes the trapeze act: Try syncing your address book or calendar between Outlook and Gmail and Yahoo! accounts. By “sync,” I mean having your information flow, in both directions, between one or more devices or databases. Make a change in one address book — on your phone, say — and that information shows up in Gmail, and Outlook.

Believe it or not, more than one internet page refers to this idea as the “Holy Grail of synchronization.”

Now, if computers can make Britney Spears a singer, could this syncing thing possibly be that complicated?

More mysteries: Sometimes I wait 15 minutes for my Treo to sync with my Mac. Sometimes it duplicates every contact in my address book, or every calendar event, or just makes multiple copies of the email addresses in each card. That’s a real laugh riot when I’m trying to get out the door. So I make backups almost every day, before I hit the sync button.

To be fair, Windows has long had nearly instantaneous sync with Windows Mobile devices. Plug a Windows-based smart phone into your computer, and pop! your data is the same on both. Apple offers a $99/year online service called .Mac (“dot Mac”) that will, albeit slowly and not dependably, keep your address book, calendar, and bookmarks synced between Macs.

Stray just a little, however, from Apple’s or Microsoft’s closed systems, and you find yourself inventing new swear words.

I have found a couple of pages that discuss methods to attain the “Holy Grail,” using software and services with snappy names like GcalDaemon, Funambol, and ScheduleWorld. I messed with GcalDaemon, and it works, but it involves command-line heavy lifting — sudo chmod -R yadda yadda — that would daunt any non-geek. Even I didn’t enjoy it.

Another semi-option is Plaxo, a useful online address book that syncs Macs and Windows with Yahoo!, but only imports one way from Gmail.

iWait

So what’s to come? Speaking of holy grails, we return to the iPhone, that obscure object of desire. We still don’t know if the damn thing works, but here’s my latest penny for the iPhone wishing pool (I’ll probably end up throwing in my Treo):

Yahoo! is offering free mobile-syncing mail accounts with the iPhone. Google has teamed with Apple to make a cool Google Maps program for the handset. I would love it if these three entities have put their brains together, and will release an open system for syncing, one in which everyone (except probably Microsoft) agrees on the fine points and plays well together.

I’ll have bunting and confetti and party hats and T-shirts that say “Sync This!” printed and waiting for the day.

(Side note: One netizen has created a contest called the “notMac Challenge,” to offer a cash prize to anyone who develops a viable and easy-to-use replacement to .Mac. Check Notmacchallenge.com for progress.) 


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