How hard is it to set up a Office Pool Web Site?
Once you input all the data (i.e. Brackets) and then set up your reports they way you'd like it's just a matter of
selecting the Reports -> Web Reports -> Build Site.
Then you just take the files that are created and upload (via an FTP client, for example) them to your Web Server.
Be sure to download and run some test scenarios so you know exactly what to expect.