How does Microsoft windows licensing work? I'd like to get a license for 5 servers, now are these license only valid per one machine or one thoughout them all? If you currently have a license, please note it in your reply with experiences.
If you have five servers, talk to an authorized Microsoft retailer about a volume licence, which should be cheaper. As mentioned, you also need CALS (client access licences) to access resources on the server from another computer. These vary depending upon what access is required (as a web server, as a file server, as a terminal services server, etc.). A server licence used to come with 5 CALs for file sharing access, but I'm not sure if it is still the case.
Microsoft licensing can be very complicated; to get the best deal you must discuss your requirements with a good retailer.