On another note, we recently went through this same process with an entire site redesign.  The executive team demanded we cut out over 75% of the pages on our site because they were useless to the visitor.  It's been 60 days since the launch of the new site and I've been able to still increase rankings, long-tail keywords, and even organic traffic.  It took a little bit of a "cowboy" mentality to get some simple things done (like using 301's instead of blocking the old content with robots.txt!).  I predicted we would lose a lot of our long tail keywords...but we haven't....yet!
Nice work Laura! This is going to be a great series. I'm working my way through SEOmoz's Advanced SEO Training Series (videos) Vol. 1 & 2 to build upon the advice and guidance that you and your team provided to me during my time at Yahoo!. Now many others will benefit from your knowledge, experience and passion for SEO strategy and tactics. Best wishes for great success in your new role.
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