After waking up at 4AM to the n-th “How do I fix the SSL problem in RailsInstaller/RubyInstaller?” in both project’s mailing lists, I stopped watching AGDQ for a couple of hours to spin up new Windows 7 virtual machines to upgrade RailsFTW to deal with those problems.
Version 0.19 is now out, with Rails 4.2.0 and RubyGems SSL fix.