Servers cost money. There are a lot of reasons to upgrade to Windows Server 2008. It is a more efficient operating system. Computers are a depreciating asset, so you are looking for a ROI that may not be there. You could do this on the cheap, and switch to Linux, but then you're going to have to bring in a Linux systems engineer/admin. No matter what, upgrading a server will cost you. One thing you could look into doing is not outsourcing your server, but doing managed hosting through a professional company. Microsoft expects Windows Server 2003 to last a long time, but its options and compatibility with Windows 7, in an enterprise environment (200 or more users) is waining. If this is for a legitimate business, you need to...