I have something of a similar nature in my home.. A Mac server and two iMacs and a Macbook Pro running off it. For this to work properly the iMac has to be running constantly, or in a state where it can be waked through Ethernet (configurable in System Preferences). To answer your questions:
1) You can do this, but it isn't automatic. You need to copy the content from the local user to the networked user, essentially creating a new user account in the process and copying all of your existing content to that. If you feel adventurous, you could try this ( http://support.apple.com/kb/HT5338 ), which is Apple's method of converting a local account to a networked one, but it doesn't require some work in the terminal, which is a little much for some people.
2) The optimal setup is where the server is the basis for all of your files, and they are simply downloaded to your Macbooks when you log in. And then any changes that are made are reflected on the server, and hence everywhere you log in.
3) Mountain Lion makes this pretty easy, and it will sync every time the laptop returns to the local network. The best directions can be found here: ( https://discussions.apple.com/thread/4154950?start=0&tstart=0 ).