Can I deploy my Django site to OS X Server?
wrt the issues above:

Yes you can. Very effectively. Just be aware that your Django sites won't integrate into Server App's GUI unless you restrict yourself to python 2.7; Apache mod_wsgi; no virtualenvs.
Not if you wish to proxy to a wsgi server like Gunicorn, because when you save the Website's panel, OS X Server will sanitise some of your essential Apache directives and you will lose control over how your Django static files, for example, are served. OS X Server has a particular execution and configuration model in mind and it does a good job of managing websites that accord with that model - but at the cost of flexibility. I know that people successully deploy Django using Apache's mod_wsgi, but that comes with severe limitations.
As in 2. The proxies section of the plist for your web app in OS X Server's ../apache2/webapp directory is all-or-nothing. e.g. You can't Include a ProxyPass /static/ ! in the right place for it to have effect.
Not with Apache mod_wsgi.
No. OS X Server 3.2.1 uses Apache 2.2. Proxies via UDS was not included in Apache until later. (Perhaps you could have Apache proxy to Nginx (via a TCP port) and, in turn, proxying to Gunicorn via each Django site's own UDS ... if you thought there was a compelling reason.)
Yes.

The approach I took:

Put your application's Apache .conf file in OS X Server's ../apache2/other directory where it will be left alone by the Server app.
Forget about trying to use the Server GUI and 'binding' web apps to sites through its Advanced settings window. A nice idea but ...
Use virtualenv(wrapper) to set up the different python and package versions for a more future-proof approach ... OS X Server 4 on Yosemite coming up!

Example code:
.conf for Django virtual server
This is adapted directly from the file that OS X Server generates from its GUI with these main differences:

ProxyPreserveHost is off by default.

ProxyPass /static/ ! prevents the Alias directive from being ignored. I found that, when including this directive using the Apple-recommended web app .plist includeFiles section, the Included lines were in the wrong place to have the desired effect.


sed your SITENAME and PORT:
&lt;VirtualHost *:80&gt;
        ServerName SITENAME
        ServerAdmin mail@you.com
        DocumentRoot &quot;/usr/local/python_projects/SITENAME&quot;
        ErrorLog /var/log/apache2/error_log
        &lt;IfModule mod_ssl.c&gt;
                SSLEngine Off
                SSLCipherSuite &quot;ALL:!aNULL:!ADH:!eNULL:!LOW:!EXP:RC4+RSA:+HIGH:+MEDIUM&quot;
                SSLProtocol -ALL +SSLv3 +TLSv1
                SSLProxyEngine On
                SSLProxyProtocol -ALL +SSLv3 +TLSv1
        &lt;/IfModule&gt;
        &lt;Directory &quot;/usr/local/python_projects/SITENAME&quot;&gt;
                Options All -Indexes -ExecCGI -Includes +MultiViews
                AllowOverride None
                &lt;IfModule mod_dav.c&gt;
                        DAV Off
                &lt;/IfModule&gt;
        &lt;/Directory&gt;
        ProxyPass         /static/ !
        Alias             /static/ /usr/local/python_projects/SITENAME/static/
        ProxyPass         /         http://localhost:PORT/
        ProxyPassReverse  /         http://localhost:PORT/
        ProxyPreserveHost On
&lt;/VirtualHost&gt;

LaunchDaemon plist for Gunicorn wsgi server
sed your SITENAME; REVERSED_SITENAME and PORT:
&lt;?xml version=&quot;1.0&quot; encoding=&quot;UTF-8&quot;?&gt;
&lt;!DOCTYPE plist PUBLIC -//Apple Computer//DTD PLIST 1.0//EN
http://www.apple.com/DTDs/PropertyList-1.0.dtd &gt;
&lt;plist version=&quot;1.0&quot;&gt;
&lt;dict&gt;
     &lt;key&gt;Label&lt;/key&gt;
     &lt;string&gt;REVERSED_SITENAME&lt;/string&gt;
     &lt;key&gt;ProgramArguments&lt;/key&gt;
     &lt;array&gt;
          &lt;string&gt;/usr/local/virtualenvs/SITENAME/bin/gunicorn&lt;/string&gt;
          &lt;string&gt;--bind=127.0.0.1:PORT&lt;/string&gt;
          &lt;string&gt;--workers=2&lt;/string&gt;
          &lt;string&gt;superlists.wsgi:application&lt;/string&gt;
     &lt;/array&gt;
     &lt;key&gt;RunAtLoad&lt;/key&gt;&lt;true/&gt;
     &lt;key&gt;WorkingDirectory&lt;/key&gt;&lt;string&gt;/usr/local/python_projects/SITENAME/source&lt;/string&gt;
&lt;!--      &lt;key&gt;StandardErrorPath&lt;/key&gt;&lt;string&gt;/var/log/gunicorn/REVERSED_SITENAME.error.log&lt;/string&gt; --&gt;     
     &lt;key&gt;KeepAlive&lt;/key&gt;&lt;true/&gt;
&lt;/dict&gt;
&lt;/plist&gt;

Snippet from the OS X Server's .bash_exports
Shows virtualenv paths specified by the virtualenvwrapper environment variables
export WORKON_HOME=/usr/local/virtualenvs
export PROJECT_HOME=/usr/local/python_projects
export VIRTUALENVWRAPPER_PYTHON=/usr/local/bin/python3
export VIRTUALENVWRAPPER_VIRTUALENV=/usr/local/bin/virtualenv
source /usr/local/bin/virtualenvwrapper.sh

Snippet from the Fabric automation file fabfile.py
Shows:

The target paths - the directories where your configuration files will end up;

The commands to activate the Django site in the final steps in deployment



# copy (and overwrite if necssary) configuration files to the LaunchDaemons and apache2/sitesdirectories

sudo('cp -f %s /Library/LaunchDaemons/%s.plist' % (gunicorn_config_file, reversed_site_name))
sudo('cp -f %s /Library/Server/Web/Config/apache2/other/%s.conf' % (apache2_config_file, site_name))

# Get the gunicorn wsgi server running on its unique TCP port 

sudo('launchctl unload -w /Library/LaunchDaemons/%s.plist' % (reversed_site_name,), warn_only=True)
sudo('launchctl load -w /Library/LaunchDaemons/%s.plist' % (reversed_site_name,))  

# Give us some assurance that the gunicorn port is open

sudo('lsof -i TCP:%s' % (port,))

# Get Apache to include the new website; talk to gunicorn; and make it available to he world!

sudo('apache2ctl graceful')