Giving MobileMe a (very quick) try
So yesterday I had enough of squinting at Windows Mobile interfaces, felt seduced by the user experience on the iPod Touch I got last February, decided it was time to treat myself (it's been hard at work during the past ten months), got my PAC from T-Mobile and I got myself an iPhone 3G.
I shall spare you the oohs and aahs (yes, I uttered many throughout the day) and skip to one point: I also signed up for MobileMe (two months free, then 59 pounds for one year, and I can unsubscribe before starting to pay) hoping that it would be the final answer to my eternal quest for perfect synchronisation of mail, contacts, calendars, photos across all devices. The idea is that all the data resides 'in the cloud' and is pushed through to all the locations you want to see it.
Well, I am about to unsubscribe to MobileMe after less than 24 hours, not because it does not do what it said it did, but because I was not prepared to change the way I work to comply with MobileMe requirements: to put it simply, I am a heavy Google user and it is not possible to use MobileMe to shadow your Google accounts.
You can read a more detailed account at MobileMe and Gmail: Pick one or expect frustration.
So I guess it's back to Gmail with IMAP (working very well so far), Google Calendar Sync with Outlook, and a simple Contacts sync with outlook via iTunes.
Although since I'm still paying for the Mail2Web Exchange account I used before switching to Gmail, one day I might try and see how that syncs with the iPhone.

