url redirect with rewrite capability

Some questions:

1. Is lion.dev.leo.world.com hosted on the same servers as bearcub.dev.leo.world.com?
2. I assume you separate requests by host header?
3. Can you see anything in the IIS logs?

Try this one and see if you see anything in the /var/log/ltm log (replace the pool with the pool for bearcub.dev.leo.world.com).

when HTTP_REQUEST {

    set host [string tolower [HTTP::host]]
    set uri [string tolower [HTTP::uri]]

    if { $host equals "lion.dev.leo.world.com" and $uri starts_with "/lookout" } { 
        HTTP::header replace Host "bearcub.dev.leo.world.com"
        pool bearcub_pool
        log local0. "Sending to the bearcub pool"
    }
}