Check out my above comment and feel free to ping me via email or twitter. Would love to get more detailed feedback from you and maybe try to change your mind!
Sorry but you're barking up the wrong tree. I use reprepro to host gpg signed packages (accessed over ssh so no ssl required) deployed from a vcs repo. The setup of the repo server itself is even handled through an apt package (hows that for self bootstrapping)
Even if I were interested, the obsession with ridiculous pricing structures means I could never use your service. Seriously how does 1 5mb package cost you more than 5 1 mb packages.
$100 a month gets me a hell of a lot of resources to host packages, and funnily enough it doesn't stop working or demand more money because the package count hit some arbitrary number.