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I sync mail, 200+ contacts (with pictures!), and calendar to Gmail (I actually use Google Applications) without a problem. I was also using the same stuff when I had a WinMo phone, and also without a problem. I'm not sure why some people are having issues with contact photos... maybe it's your version of Outlook? You should be able to sync your Outlook contacts and calendar up to Gmail using Exchange protocols.

I successfully dumped a LOT of old mail into Gmail, but I also don't keep old e-mails with large attachments.