I wasted a silly amount of time today trying to get Windows Live Contacts/Calendar to sync with MobileMe (and the iPhone) via Outlook and the new Outlook Connector 12.1 beta. (Long story short: While you can, in fact, make your Windows Live data store the default in Outlook via Account Settings, Apple’s sync utility requires a Unicode-based PST file, and the Windows Live data store does not qualify or work at all. I’ll keep plugging away.) But what about Google’s Gmail Contacts and Google Calendar? This might be a good solution if push-style updating of the iPhone is a concern:

NuevaSync allows direct, over-the-air, native synchronization of certain smart phones and PDA devices with public PIM, and calendaring services including Google Calendar. NuevaSync does not need any software installed on your device because it uses synchronization protocols that are already built in.

Supported Devices - Apple iPhone 2.0, iPhone 3G and iPod touch 2.0; Windows Mobile based PDAs and smartphones.

Supported Services - Google Calendar for calendar events; Google Contacts / GMail for contacts; Plaxo for contacts.

Thanks Tristan H. for the tip.