Update:

I finally managed to sort of deploy this environment.
As a result, I nailed this one down to the SSL/TLS certificate. Maybe I didn't understand something.

If I reset the environment(this was apparently required), set the hostname, choose self-signed option. The cloud deploy's fine.
As soon as I go to add my own pem file, deployment breaks.

I use a Class 1 Certificate from StartSSL.com and I believe it's working correctly except for:

2016-09-14 01:15:34	NOTICE	 Finished catalog run in 25.32 seconds
2016-09-14 01:15:34	WARNING	 (/Stage[main]/Openstack_tasks::Openstack_network::Networks/Neutron_subnet[admin_floating_net__subnet]) Skipping because of failed dependencies
2016-09-14 01:15:34	NOTICE	 (/Stage[main]/Openstack_tasks::Openstack_network::Networks/Neutron_subnet[admin_floating_net__subnet]) Dependency Neutron_network[admin_floating_net] has failures: true
2016-09-14 01:15:34	WARNING	 (/Stage[main]/Openstack_tasks::Openstack_network::Networks/Neutron_subnet[admin_internal_net__subnet]) Skipping because of failed dependencies
2016-09-14 01:15:34	NOTICE	 (/Stage[main]/Openstack_tasks::Openstack_network::Networks/Neutron_subnet[admin_internal_net__subnet]) Dependency Neutron_network[admin_internal_net] has failures: true
2016-09-14 01:15:34	ERR	 /usr/bin/puppet:8:in `<main>'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/util/command_line.rb:92:in `execute'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/util/command_line.rb:146:in `run'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application.rb:381:in `run'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/util.rb:496:in `exit_on_fail'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application.rb:381:in `block in run'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application.rb:507:in `plugin_hook'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application.rb:381:in `block (2 levels) in run'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application/apply.rb:159:in `run_command'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application/apply.rb:198:in `main'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet.rb:246:in `override'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/context.rb:64:in `override'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application/apply.rb:236:in `block in main'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/application/apply.rb:302:in `apply_catalog'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/configurer.rb:133:in `run'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet.rb:246:in `override'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/context.rb:64:in `override'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/configurer.rb:134:in `block in run'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/configurer.rb:227:in `run_internal'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/configurer.rb:119:in `apply_catalog'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/util.rb:160:in `benchmark'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/1.9.1/benchmark.rb:295:in `realtime'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/util.rb:161:in `block in benchmark'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/configurer.rb:120:in `block in apply_catalog'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/resource/catalog.rb:168:in `apply'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/transaction/report.rb:112:in `as_logging_destination'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/util/log.rb:149:in `with_destination'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/resource/catalog.rb:169:in `block in apply'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/transaction.rb:138:in `evaluate'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/graph/relationship_graph.rb:116:in `traverse'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/graph/relationship_graph.rb:116:in `call'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/transaction.rb:96:in `block in evaluate'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/transaction.rb:197:in `prefetch_if_necessary'
2016-09-14 01:15:34	ERR	 /usr/lib/ruby/vendor_ruby/puppet/transaction.rb:307:in `prefetch'
2016-09-14 01:15:34	ERR	 /etc/puppet/modules/neutron/lib/puppet/provider/neutron_subnet/neutron.rb:57:in `prefetch'
2016-09-14 01:15:34	ERR	 /etc/puppet/modules/neutron/lib/puppet/provider/neutron_subnet/neutron.rb:33:in `instances'
2016-09-14 01:15:34	ERR	 /etc/puppet/modules/neutron/lib/puppet/provider/neutron.rb:139:in `list_neutron_resources'
2016-09-14 01:15:34	ERR	 Could not prefetch neutron_subnet provider 'neutron': Can't retrieve subnet-list because Neutron or Keystone API is not available.
2016-09-14 01:15:31	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) SSL exception connecting to https://example.com:9696/v2.0/subnets.json: [Errno 1] _ssl.c:510: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed". Retrying for 1 sec.
2016-09-14 01:15:31	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   InsecurePlatformWarning
2016-09-14 01:15:31	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:120: InsecurePlatformWarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately and may cause certain SSL connections to fail. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning.
2016-09-14 01:15:31	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   SNIMissingWarning
2016-09-14 01:15:31	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) Unable to complete neutron request due to non-fatal error: "Execution of '/usr/bin/neutron subnet-list --format=csv --column=id --quote=none' returned 1: /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:315: SNIMissingWarning: An HTTPS request has been made, but the SNI (Subject Name Indication) extension to TLS is not available on this platform. This may cause the server to present an incorrect TLS certificate, which can cause validation failures. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#snimissingwarning.
2016-09-14 01:15:28	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) SSL exception connecting to https://example.com:9696/v2.0/subnets.json: [Errno 1] _ssl.c:510: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed". Retrying for 4 sec.
2016-09-14 01:15:28	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   InsecurePlatformWarning
2016-09-14 01:15:28	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:120: InsecurePlatformWarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately and may cause certain SSL connections to fail. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning.
2016-09-14 01:15:28	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   SNIMissingWarning
2016-09-14 01:15:28	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) Unable to complete neutron request due to non-fatal error: "Execution of '/usr/bin/neutron subnet-list --format=csv --column=id --quote=none' returned 1: /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:315: SNIMissingWarning: An HTTPS request has been made, but the SNI (Subject Name Indication) extension to TLS is not available on this platform. This may cause the server to present an incorrect TLS certificate, which can cause validation failures. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#snimissingwarning.
2016-09-14 01:15:25	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) SSL exception connecting to https://example.com:9696/v2.0/subnets.json: [Errno 1] _ssl.c:510: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed". Retrying for 7 sec.
2016-09-14 01:15:25	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   InsecurePlatformWarning
2016-09-14 01:15:25	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:120: InsecurePlatformWarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately and may cause certain SSL connections to fail. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning.
2016-09-14 01:15:25	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   SNIMissingWarning
2016-09-14 01:15:25	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) Unable to complete neutron request due to non-fatal error: "Execution of '/usr/bin/neutron subnet-list --format=csv --column=id --quote=none' returned 1: /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:315: SNIMissingWarning: An HTTPS request has been made, but the SNI (Subject Name Indication) extension to TLS is not available on this platform. This may cause the server to present an incorrect TLS certificate, which can cause validation failures. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#snimissingwarning.
2016-09-14 01:15:22	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) SSL exception connecting to https://example.com:9696/v2.0/subnets.json: [Errno 1] _ssl.c:510: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed". Retrying for 10 sec.
2016-09-14 01:15:22	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   InsecurePlatformWarning
2016-09-14 01:15:22	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:120: InsecurePlatformWarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately and may cause certain SSL connections to fail. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning.
2016-09-14 01:15:22	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron)   SNIMissingWarning
2016-09-14 01:15:22	NOTICE	 (Puppet::Type::Neutron_subnet::ProviderNeutron) Unable to complete neutron request due to non-fatal error: "Execution of '/usr/bin/neutron subnet-list --format=csv --column=id --quote=none' returned 1: /usr/lib/python2.7/dist-packages/urllib3/util/ssl_.py:315: SNIMissingWarning: An HTTPS request has been made, but the SNI (Subject Name Indication) extension to TLS is not available on this platform. This may cause the server to present an incorrect TLS certificate, which can cause validation failures. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#snimissingwarning.
2016-09-14 01:15:22	ERR	 (/Stage[main]/Openstack_tasks::Openstack_network::Networks/Neutron_network[admin_internal_net]/ensure) change from absent to present failed: Not managing Neutron_network[admin_internal_net] due to earlier Neutron API failures.