Multiple domains, multiple vhosts, separate rails apps - ruby-on-rails

Question

I am trying to host multiple different rails apps on the same VPS using multiple domains. I am using Apache 2.2.17 on Ubuntu 10.10. For Apache, I have multiple vhost files so that I can enable and disable particular sites easily without needing to comment them out or delete them. In addition, I am also using mod_rewrite so that the multiple domains that go to the same rails app appear to go to the same URL so I don't take a hit with search engines as far as duplicate content.
I believe that my DNS is setup properly. For each of the domains, I have a www subdomain as well as some site-specific sub-domains, such as blogs, etc. The issue I am seeing is that Apache appears to matching the www subdomain immediately and not examining the additional URL behind it. Changing ServerAlias does nothing. For example, using my setup, if I enter davidheartsrachel.com, I properly reach my wedding website. However, if I use www.davidheartsrachel.com, I reach my other website, my software development business. The URL is not re-written; it stays as davidheartsrachel.com instead of afewguyscoding.com.
The only way I have been able to properly get it to work is to use mod_rewrite in the primary vhost file to redirect to the wedding website vhost file (you can see that I have that in the primary vhost file, but it is commented out for purposes of this question). This doesn't seem proper to me? Should I get another IP and do IP vhosts instead of name-based vhosts?
When I execute apachectl -S, I get the following:
VirtualHost configuration:
wildcard NameVirtualHosts and _default_ servers:
*:80 is a NameVirtualHost
default server afewguyscoding.com (/etc/apache2/sites-enabled/afewguyscoding.com:1)
port 80 namevhost afewguyscoding.com (/etc/apache2/sites-enabled/afewguyscoding.com:1)
port 80 namevhost blog.afewguyscoding.com (/etc/apache2/sites-enabled/afewguyscoding.com:69)
port 80 namevhost lbbs.afewguyscoding.com (/etc/apache2/sites-enabled/afewguyscoding.com:84)
port 80 namevhost davidheartsrachel.com (/etc/apache2/sites-enabled/davidheartsrachel.com:1)
port 80 namevhost dhr.afewguyscoding.com (/etc/apache2/sites-enabled/davidheartsrachel_staging:1)
Syntax OK
I notice that afewguyscoding.com is the default site - however, doesn't it have to do a full string match to determine the proper site?
Primary site's vhost file
<VirtualHost *:80>
ServerAdmin david.stites#afewguyscoding.com
ServerName afewguyscoding.com
ServerAlias davidstites.com, 5280software.com, milehigh-software.com, milehighsoftware.org
ServerAlias www.5280software.com, www.milehigh-software.com, www.milehighsoftware.org, www.davidstites.com, www.afewguyscoding.com
# this tells rails that it will run in production mode
# this is for rails < 3.x
RailsEnv production
DocumentRoot /var/www/afewguyscoding/current/public
DirectoryIndex index.html
# custom log file locations
# possible values include: debug, info, notice, warn, error, crit,
# alert, emerg.
LogLevel alert
ErrorLog /var/www/afewguyscoding/current/log/error.log
CustomLog /var/www/afewguyscoding/current/log/access.log combined
# allows compression of text based mime.types
AddOutputFilterByType DEFLATE text/html text/plain text/xml text/javascript text/css application/x-javascript
BrowserMatch ^Mozilla/4 gzip-only-text/html
BrowserMatch ^Mozilla/4\.0[678] no-gzip
BrowserMatch \bMSIE !no-gzip !gzip-only-text/html
FileETag None
RewriteEngine On
# check for maintenance file and redirect all requests
RewriteCond %{DOCUMENT_ROOT}/system/maintenance.html -f
RewriteCond %{REQUEST_URI} !\.(css|jpg|png|gif)$
RewriteCond %{REQUEST_URI} !^/ws/
RewriteCond %{SCRIPT_FILENAME} !maintenance.html
RewriteRule ^.*$ /system/maintenance.html
#RewriteCond %{HTTP_HOST} ^www.davidheartsrachel.com$
#RewriteRule ^(.*)$ http://davidheartsrachel.com$1 [L]
RewriteCond %{HTTP_HOST} ^www.davidstites.com$
RewriteRule ^(.*)$ http://www.afewguyscoding.com$1 [R=301,L]
<Directory /var/www/afewguyscoding/current/public>
Options Indexes FollowSymLinks MultiViews
AllowOverride All
Order allow,deny
allow from all
</Directory>
# In case I ever need CGI
#ScriptAlias /cgi-bin/ /usr/lib/cgi-bin/
#<Directory "/usr/lib/cgi-bin">
# AllowOverride None
# Options +ExecCGI -MultiViews +SymLinksIfOwnerMatch
# Order allow,deny
# Allow from all
#</Directory>
# how we can restrict access to documents from the local subnet
#Order deny,allow
#Deny from all
#Allow from 127.0.0.0/255.0.0.0 ::1/128
<Location /blog>
PassengerEnabled off
</Location>
</VirtualHost>
<VirtualHost *:80>
ServerAdmin info#afewguyscoding.com
ServerName blog.afewguyscoding.com
DocumentRoot /var/www/wpress
DirectoryIndex index.php
<Directory /var/www/afewguyscoding/current/public>
Options Indexes FollowSymLinks MultiViews
AllowOverride All
Order allow,deny
allow from all
</Directory>
</VirtualHost>
Wedding site's vhost file
<VirtualHost *:80>
ServerAdmin info#davidheartsrachel.com
ServerName davidheartsrachel.com
ServerAlias rachelanddavid.net, rachelanddavidstites.com, rachelanddavidwedding.com
ServerAlias www.davidheartsrachel.com, www.rachelanddavidstites.com, www.rachelanddavidwedding.com, www.rachelanddavid.net
# this tells rails that it will run in production mode
# this is for rails < 3.x
RailsEnv production
# this is for rails >= 3.x
RackEnv production
DocumentRoot /var/www/davidheartsrachel/current/public
DirectoryIndex index.html
# Custom log file locations
# Possible values include: debug, info, notice, warn, error, crit, alert and emerg,
LogLevel alert
ErrorLog /var/www/davidheartsrachel/current/log/error.log
CustomLog /var/www/davidheartsrachel/current/log/access.log combined
# Allows compression of text based mime types
AddOutputFilterByType DEFLATE text/html text/plain text/xml text/javascript text/css application/x-javascript
BrowserMatch ^Mozilla/4 gzip-only-text/html
BrowserMatch ^Mozilla/4\.0[678] no-gzip
BrowserMatch \bMSIE !no-gzip !gzip-only-text/html
FileETag None
RewriteEngine On
# Check for maintenance file and redirect all requests
RewriteCond %{DOCUMENT_ROOT}/system/maintenance.html -f
RewriteCond %{REQUEST_URI} !\.(css|jpg|png|gif)$
RewriteCond %{SCRIPT_FILENAME} !maintenance.html
RewriteRule ^.*$ /system/maintenance.html [L]
RewriteCond %{HTTP_HOST} ^www.rachelanddavidwedding.com$
RewriteRule ^(.*)$ http://www.davidheartsrachel.com$1 [R=301,L]
RewriteCond %{HTTP_HOST} ^www.rachelanddavidstites.com$
RewriteRule ^(.*)$ http://www.davidheartsrachel.com$1 [R=301,L]
# Static cache
RewriteCond %{REQUEST_METHOD} !^POST$
RewriteCond /var/www/davidheartsrachel/current/tmp/cache/static$1/index.html -f
RewriteRule ^(.*)$ /var/www/davidheartsrachel/current/tmp/cache/static$1/index.html [L]
<Directory /var/www/davidheartsrachel/current/public>
Options Indexes FollowSymLinks MultiViews
AllowOverride All
Order allow,deny
Allow from All
</Directory>
</VirtualHost>
If you can think of any more information that might be helpful, please, ask me to post it.
Edit:
Let me try to clear this up. In the most essential form, my question is: why does going to davidheartsrachel.com takes you to www.afewguyscoding.com and davidheartsrachel.com takes you to davidheartsrachel.com based on my configuration above

Answer 1

On my servers I don't define a primary site in my main httpd.conf file. I do all the virtual hosting in separate application specific conf files.
The only thing I have in my main httpd.conf is the line NameVirtualHost *:80
Here's a gist of a way you could try it. I pulled all the wedding site configuration out of your main site configuration. I set it so davidstites.com, afewguyscoding.com, and www.davidstites.com all redirect to www.afewguyscoding.com. The other domains (milehigh et al) are unaffected. I'm not sure where you wanted those to go.
All the wedding related domains redirect to www.davidheartsrachel.com.
I did notice what I think might have been a mess up in your main site configuration. Toward the end where you set your directory permissions you were using the /var/www/afewguyscoding/current/public directory instead of the /var/www/wpress that is the DocumentRoot. The correction I made there is on line 74 of the first document in that gist.

Answer 2

The answer is that I was incorrectly separating the entries under ServerAlias with a comma thusly:
ServerAlias rachelanddavid.net, rachelanddavidstites.com, rachelanddavidwedding.com, www.davidheartsrachel.com, www.rachelanddavidstites.com, www.rachelanddavidwedding.com, www.rachelanddavid.net
It is supposed to be a space:
ServerAlias rachelanddavid.net rachelanddavidstites.com rachelanddavidwedding.com www.davidheartsrachel.com www.rachelanddavidstites.com www.rachelanddavidwedding.com www.rachelanddavid.net