Upgrade Windows Server 2000 to 2k3+

My boss is wanting me to upgrade our server at work from Windows 2k to 2k3 or later. I came into the company AFTER the windows setup and if I had it my way we would be running Ubuntu Server. Anyway, my question here is when upgrading from 2k to 2k3 will my settings be saved and restored as well as my programs? All the server is doing is a simple vpn fileshare to around 40 users around the country. I would like this to be as seamless as possible but I don't want to take down the entire server and reinput all my vpn settings that are already established. Thoughts?
 
Back