My Evo will be delivered tomorrow.
I use Gmail through Outlook on my PC, and have been using ActiveSync and then WMDC to sync with all of my WM phones. However, that did nothing to sync my contacts and calendar with Gmail on Google.
On a whim, I set up Google Sync on my phone like this:
Setting Up Your Windows Mobile Phone for Google Sync : Google Sync - Google Mobile Help. I selected Email, Calendar, and Contacts to sync and it worked like a charm, Contact pictures and all!
Now when my Evo shows up tomorrow, I'll just enter my Gmail credentials on it, and all will be sync'd back to the new phone. I'll be able to use HTC Sync for the PC to phone part, so you're on your own for that.