I was wondering whether syning with the pocket pc is similar to syncing with the Palm OS Documents to GO?

Specifically, can I set up my Active Sync so that certain documents (like Word documents) are updated automatically?

Sure, just enable Files syncing in ActiveSync on the PC - (under Tools->Options). This will create a "My Documents" folder for your PPC on your desktop. Files in the My Documents folders on your Axim will automatically be transferred to the desktop folder the next time you sync, and files you place in the desktop folder will be copied over to the Axim. If there is a sync conflict (a file was altered both on the desktop and the PPC since the last sync), it will let you choose which file should overwrite the other.