Changes that made it work for me, mostly

Vagrantfile

@@ -1,50 +1,24 @@
 # -*- mode: ruby -*-
 # vi: set ft=ruby :
 
-Vagrant::Config.run do |config|
-  # All Vagrant configuration is done here. The most common configuration
-  # options are documented and commented below. For a complete reference,
-  # please see the online documentation at vagrantup.com.
-
-  username      = "ubuntu"
+Vagrant.configure("2") do |config|
   local_app_dir = "/Users/ted/dc/documentcloud/"
-  app_root      = "/home/#{username}/documentcloud"
+  app_root      = "/home/vagrant/documentcloud"
   rails_env     = "development"
 
-  # Every Vagrant virtual environment requires a box to build off of.
-  config.vm.box = "documentcloud"
-  config.ssh.username = username
+  config.vm.box = "ubuntu/trusty64"
+  config.vm.network :private_network, ip: "192.168.33.10"
+  config.vm.synced_folder local_app_dir, app_root
 
-  # The url from where the 'config.vm.box' box will be fetched if it
-  # doesn't already exist on the user's system.
-  # config.vm.box_url = "http://domain.com/path/to/above.box"
-
-  # Assign this VM to a host-only network IP, allowing you to access it
-  # via the IP. Host-only networks can talk to the host machine as well as
-  # any other machines on the same network, but cannot be accessed (through this
-  # network interface) by any external networks.
-  config.vm.network :hostonly, "192.168.33.10"
-
-  # Assign this VM to a bridged network, allowing you to connect directly to a
-  # network using the host's network device. This makes the VM appear as another
-  # physical device on your network.
-  # config.vm.network :bridged
-
-  # Forward a port from the guest to the host, which allows for outside
-  # computers to access the VM, whereas host only networking does not.
-  # config.vm.forward_port 80, 8080
-
-  # Share an additional folder to the guest VM. The first argument is
-  # an identifier, the second is the path on the guest to mount the
-  # folder, and the third is the path on the host to the actual folder.
-  # config.vm.share_folder "v-data", "/vagrant_data", "../data"
-  config.vm.share_folder "app_root", app_root, local_app_dir
+  config.vm.provider "virtualbox" do |v|
+    v.memory = 2048
+  end
 
   script = <<-SHELL
-    export USERNAME=#{username};
+    export USERNAME=vagrant;
     export RAILS_ENV=#{rails_env};
     sh /vagrant/scripts/base.sh;
 SHELL
 
-  config.vm.provision :shell, :inline => script
+  config.vm.provision :shell, inline: script
 end

scripts/app.sh

@@ -1,6 +1,6 @@
 # Ensure nginx is installed
-test -e /usr/local/nginx || /usr/local/bin/passenger-install-nginx-module --auto --auto-download \
-    --prefix /usr/local/nginx --extra-configure-flags='--with-http_gzip_static_module --with-http_ssl_module --with-http_stub_status_module'
+test -e /usr/local/nginx || (gem install passenger && /usr/local/bin/passenger-install-nginx-module --auto --auto-download \
+    --prefix /usr/local/nginx --extra-configure-flags='--with-http_gzip_static_module --with-http_ssl_module --with-http_stub_status_module')
 
 LINE='export PATH=$PATH:/usr/local/nginx/sbin'
 grep -q "$LINE" .bashrc 2>/dev/null || echo "$LINE" >> .bashrc
@@ -10,10 +10,6 @@ mkdir -p /var/log/nginx
 
 ruby /vagrant/scripts/configure_nginx.rb
 
-cd /home/ubuntu/documentcloud
-
-test -e secrets/keys || { cp -r config/server/keys secrets/ ; }
-
-cp config/server/nginx/nginx.init /etc/init.d/nginx
+cp /home/vagrant/documentcloud/config/server/files/nginx/nginx.init /etc/init.d/nginx
 update-rc.d nginx defaults
 /etc/init.d/nginx start

scripts/base.sh

@@ -6,7 +6,7 @@ test $USERNAME  || { echo "USERNAME has to be set" >&2; exit 1; }
 test $RAILS_ENV || { echo "USERNAME has to be set" >&2; exit 1; }
 
 # Set up system dependencies
-BASICS='git build-essential postgresql libpq-dev git sqlite3 libsqlite3-dev libpcre3-dev lzop libxml2-dev libxslt-dev libcurl4-gnutls-dev libitext-java ruby1.8 rubygems'
+BASICS='git build-essential postgresql postgresql-contrib libpq-dev git sqlite3 libsqlite3-dev libpcre3-dev lzop libxml2-dev libxslt-dev libcurl4-gnutls-dev libitext-java ruby ruby-dev'
 echo $BASICS | xargs apt-get install -y
 
 DOCSPLIT_DEPS='graphicsmagick pdftk xpdf poppler-utils libreoffice libreoffice-java-common tesseract-ocr ghostscript'
@@ -21,22 +21,22 @@ grep -q github .ssh/known_hosts 2>/dev/null || ssh-keyscan -t rsa github.com > .
 
 # Install gems
 cd documentcloud
-git checkout --track -b bundler origin/bundler
-git pull
+#git checkout --track -b bundler origin/bundler
+#git pull
 gem install bundler --no-ri --no-rdoc
 bundle install
-git checkout master
-git pull
+#git checkout master
+#git pull
 
 # Ensure that the secrets directory exists
-test -e secrets || { cp -r config/server/secrets ./secrets; }
+test -e secrets || { cp -r config/server/files/secrets ./secrets; }
 
 # disable ssh dns to avoid long pause before login
 grep -q '^UseDNS no' /etc/ssh/sshd_config || echo 'UseDNS no' >> /etc/ssh/sshd_config
 /etc/init.d/ssh reload
 
 # replace annoying motd with new one
-rm /etc/motd
+rm -f /etc/motd
 cat >/etc/motd <<'EOF'
 
 ______                                      _   _____ _                 _

scripts/configure_nginx.rb

@@ -1,10 +1,10 @@
 require 'fileutils'
 require 'erb'
 =begin
-  cp config/server/nginx/nginx.conf /usr/local/nginx/conf/
-  cp config/server/nginx/$RAILS_ENVIRONMENT.conf /usr/local/nginx/conf/sites-enabled/
+  cp config/server/files/nginx/nginx.conf /usr/local/nginx/conf/
+  cp config/server/files/nginx/$RAILS_ENVIRONMENT.conf /usr/local/nginx/conf/sites-enabled/
   # TODO nginx configuration is not rock solid
-  cp config/server/nginx/nginx.init /etc/init.d/nginx
+  cp config/server/files/nginx/nginx.init /etc/init.d/nginx
   update-rc.d nginx defaults
 =end
 
@@ -18,16 +18,16 @@
 end
 
 File.open "/usr/local/nginx/conf/sites-enabled/#{rails_env}.conf", "w" do |site_conf|
-  certpath = "/home/ubuntu/documentcloud/secrets/keys/dev.dcloud.org.crt"
-  keypath  = "/home/ubuntu/documentcloud/secrets/keys/dev.dcloud.org.key"
+  certpath = "/home/vagrant/documentcloud/secrets/keys/dev.dcloud.org.crt"
+  keypath  = "/home/vagrant/documentcloud/secrets/keys/dev.dcloud.org.key"
 
   site_conf_template = File.open(File.join(here, "erb", "site.conf.erb")).read
   site_conf.puts ERB.new(site_conf_template).result(binding)
 end
 
 File.open "/usr/local/nginx/conf/documentcloud.conf", "w" do |dc_conf|
   server_name = "dev.dcloud.org"
-  app_root    = "/home/ubuntu/documentcloud/public"
+  app_root    = "/home/vagrant/documentcloud/public"
 
   dc_conf_template = File.open(File.join(here, "erb", "documentcloud.conf.erb")).read
   dc_conf.puts ERB.new(dc_conf_template).result(binding)

scripts/db.sh

@@ -1,13 +1,13 @@
 # verify that postgres is loaded properly
 
-test $USERNAME || { USERNAME=ubuntu; }
+test $USERNAME || { USERNAME=vagrant; }
 
-test -e /etc/postgresql/9.1/main/pg_hba.conf || { echo "Can't find the PostgreSQL 9.1 Client Authentication Configuration File (/etc/postgresql/9.1/main/pg_hba.conf)" >&2; exit 1; }
+test -e /etc/postgresql/9.3/main/pg_hba.conf || { echo "Can't find the PostgreSQL 9.3 Client Authentication Configuration File (/etc/postgresql/9.3/main/pg_hba.conf)" >&2; exit 1; }
 
 cd /home/$USERNAME/documentcloud
 
 # setup dummy postgres environment so that you can verify rails is working
-cp config/server/postgres/pg_hba.conf  /etc/postgresql/9.1/main/pg_hba.conf
+cp config/server/files/postgres/pg_hba.conf /etc/postgresql/9.3/main/pg_hba.conf
 /etc/init.d/postgresql reload
 
 # verify that databases don't already exist
@@ -27,7 +27,8 @@ sudo -u postgres createdb dcloud_analytics_$RAILS_ENV
 echo "CREATE EXTENSION hstore;" | sudo -u postgres psql dcloud_$RAILS_ENV
 
 # import development schema to dcloud_#{env} and analytics schema to dcloud_analytics_#{env}
-sudo -u postgres psql -f db/development_structure.sql dcloud_$RAILS_ENV 2>&1|grep ERROR
+#sudo -u postgres psql -f db/development_structure.sql dcloud_$RAILS_ENV 2>&1|grep ERROR
+sudo -u postgres psql -f db/structure.sql dcloud_$RAILS_ENV 2>&1|grep ERROR
 sudo -u postgres psql -f db/analytics_structure.sql dcloud_analytics_$RAILS_ENV 2>&1|grep ERROR
 
 rake db:migrate

scripts/erb/nginx.conf.erb

@@ -10,7 +10,7 @@ events {
 
 http {
   passenger_root <%= passenger_root %>;
-  passenger_ruby /usr/bin/ruby1.8;
+  passenger_ruby /usr/bin/ruby;
   passenger_default_user www-data;
   passenger_pool_idle_time 0;
   passenger_max_pool_size 4;