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Good Evening SIMbiz! That's a really interesting question.  I would imagine the closer the URL to exact keyword match, the better. However a couple extra characters should not be too detrimental, especially if those extra characters are a nonsensical string of letters or a short string of numbers.  One issue I've run into in the past, which you're probably way smarter and would never do something like this, is the creation of very similar (aka duplicate) content pages as a means to have a static page for each unique referrer site. Later to learn how to clean up the link juice cannibalization with canonicalization. For which I found this page very handy: http://www.seomoz.org/learn-seo/canonicalization -- Hope it helps.  Best, Evan

Good Evening Macky7! I was reading a great post earlier tonight, by Paddy Moogan: 301 Redirect or Rel=Canonical - Which One Should You Use? http://www.seomoz.org/blog/301-redirect-or-relcanonical-which-one-should-you-use (Even Matt Cutts weighs in on the issue!) Within the post, I quote: "Is there another page on the site which has very similar content that you could send the user to?  If so, use a 301 and point it to the similar page so that you stand a chance of retaining the traffic you already get" From what I gather in your question, I'd probably: 1.) 301 as many "very similar" pages as possible from site 1 to site 2 2.) 301 the remaining pages of site 1 to site 2's homepage  Best, Evan