So basically can drupal satisfy my requirements for file uploads and pages both?
Yes, Drupal is a highly modular system with modules for nearly every requirement. You should meet most if not all of your requirements with a standard installation of Drupal (especially with the upcoming Drupal 7).
Here are some links which should get you going: http://drupal.org/start http://drupal.org/documentation, especially http://drupal.org/node/257
A great site for looking for Drupal modules is http://drupalmodules.com
File Management: http://drupalmodules.com/m?c=File%2Bmanagement
hth Frank