Sharing files can be a pain. The larger the file is, the more difficulty it inevitably creates. If you want those files kept private, you're in for a real nightmare. Well, not exactly.
Onionshare is a relatively new application that allows you to share files of any size securely and relatively anonymously over the Tor network without the need for a "midde-man" website. It's completely free and open source, and it's actually easy for anyone to use.