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1. What is the best practice to route URL's to its unique landing page prior to client login?What you need is virtual hosting.
See http://www.liferay.com/web/guest/community/wiki/-/wiki/Main/High%20Availability%20Guide#section-High+Availability+Guide-TheBigPicture for details.
2. From a webserver perspective, what are the options to route URL requests to the appropriate Web Space "entry points" i.e. would one set this up in Apache, Glassfish, or Web Space and how?See my first comment. It can be handled in the web server(tomcat)
3. What are the options to customise each landing page to have its own unique look and feel?Each community can have its own look and feel.
See http://docs.sun.com/app/docs/doc/820-7054/ghycy?a=view to know how to do this.