If you want to add capabilities to any role site-wide, here is a script to help out. Drop the script in the wp-admin folder and make sure to login as admin, then just run the script from your browser.
<?php
require_once('admin.php');
// Add roles you want to modify here.
$roles = Array("contributor");
// Capabilities to add to each role here.
$caps = Array("upload_files");
$blogs = get_blog_list(0, 'all');
foreach($blogs as $blog)
{
switch_to_blog($blog['blog_id']);
foreach ($roles as $role)
{
$r = get_role($role);
foreach($caps as $cap)
{
$r->add_cap($cap);
}
print "Finished adding capabilities: " . implode(',', $caps) . " to role '$role' on blog {$blog['path']}<br/>";
}
restore_current_blog();
}
?>