A friend and I work on computers as a hobby and it’s a hassle and expensive to keep burning cds with the stuff we need. We want to be able to log into the server download and upload files we need. Is there a set of software I can use to build a file server accessible from remote locations? If possible I would like something web browser friendly and not a hassle to setup and maintain. Windows based server is preferred but not essential.

It sounds like you want FTP software. I'm sure you'll find some on the web.