First of all, avoid WordPress because (a) it wasn't designed for subscriptions and datasets and (b) it has a history of security issues [1] As bmelton said, Ra

First of all, avoid WordPress because (a) it wasn't designed for subscriptions and datasets and (b) it has a history of security issues [1] As bmelton said, Rails is a good option. If you're going to use Rails, my advice wrt security would be: - Don't try and roll your own authentication system. Use Devise and keep it and Rails updated. - Run the entire app over SSL - Use best practices to secure the actual box where your app runs. Assuming *nix, this means things like disabling root login, using fail2ban, iptables, key-based login, - Make sure to do some basic security setup on your database if it's on the same box. Allow only local connections, run mysql_secure_installation, etc. For learning Rails, I'd suggest going through the Rails Tutorial from Michael Hartl [2] and/or getting a RailsCasts subscription [3] and/or trying one-month rails [4] [1] http://www.cvedetails.com/vulnerability-list/vendor_id-2337/product_id-4096/ http://www.cvedetails.com/vulnerability-list/vendor_id-2337/... [2] http://ruby.railstutorial.org/ http://ruby.railstutorial.org/ [3] http://railscasts.com http://railscasts.com [4] https://onemonthrails.com https://onemonthrails.com