I highly doubt this is easily possible, but I thought I'd ask anyway.

Is it at all possible to restrict file downloads to users in a certain group? I have sensitive documents that I'd like to upload and store in a member's section, and then only allow members that are logged into their specific group to be able to download them.

The site currently uses another CMS but I'd like to import it over to SS, but this feature doesn't seem possible. Any ideas or work arounds?

I'm not sure just disabling the directory listing of files will be enough. These are financial documents related to companies, so they won't be sharing the links to the files, but they need peace of mind knowing nobody else can access them.