How often should you redesign your site?
mikeryan: I'd say 5-7 years would be time to start looking at an entire overhaul.Here's the thing.  Your site should be in constant state of flux with new features added and subtracted, moved etc. After a while you'll just end up with a bit of code "crud". Its almost worth it just to do a site wide front end rewrite once every 3 years or so.  I think 5-7 years is about the amount of time that it takes for a styles to change enough where your site will start to get a bit stale.