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.
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:
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: