This works:
<VirtualHost *>
<Directory /Users/jwalker/dev/test>
AllowOverride All
</Directory>
ServerAdmin jason@coolbluei.com
DocumentRoot /Users/jwalker/dev/test
ServerName test.jwalker.coolbluebeta.com
</VirtualHost>
This does not (causes "mod_rewrite: maximum number of internal redirects reached. Assuming configuration error. Use 'RewriteOptions MaxRedirects' to increase the limit if neccessary." error):
<Directory /Users/*>
AllowOverride All
</Directory>
VirtualDocumentRoot /Users/%2/dev/%1