Is it possible to have 2 web servers running on the same box with different ports and then use htaccess to tunnel traffic from 1 server to another based on a rewritecond? Basically when a certain condition is met I want the request to be handled by my other web server and I don't want to return a moved response.
Yes, it's possible. If the first server is Apache, you can use it as a reverse proxy using mod_proxy to do this.
http://httpd.apache.org/docs/2.0/mod/mod_proxy.html#proxypass
If your proxy requirement is more complex, you can also tell mod_rewrite to send the substitution part of the rewrite rule to mod_proxy with the "P" flag:
It appears (I'm not familiar with litespeed) that the litespeed rewrite engine is identical to Apache:
http://www.litespeedtech.com/docs/webserver/config/rewrite/
So to test for the absence of a cookie, you'd use a Rewrite rule like so:
There's an example of litespeed rewrite+proxy here:
http://www.litespeedtech.com/support/forum/showthread.php?t=2879