Shawn, this sounds like quite an involved process you're going through --as it should be. As long as you're undertaking the makeover, it's a good idea to do it thoroughly and carefully. I'm glad to hear that you got some usability feedback during the design stages, instead of after the launch as many other sites do.
I'd love to see "before and after" pictures. I've always loved looking at house remodels and comparing the drab 'before' with the energized 'after.' I hope you'll at least share a link to your new site when it's ready for prime time.

Also, I'm sure others would like to know about the "better calendar tools" and the trials and tribulations of migrating content. Keep us posted!