Broadway - 1:33 am on Jun 19, 2013 (gmt 0)
This turned out to be super easy.
Started with a new host.
I just installed Drupal in my root.
Uploaded all my static HTML pages to their original subdirectories in the root.
Set the default handler in .htaccess:
DirectoryIndex index.htm index.php index.html
Done! Zero (new) redirects.
Apache looks for static html URL's first, if it can't find the URL it looks to Drupal.
Now I can convert pages at will. As they're converted to Drupal I just delete their .htm verson, apache defaults to Drupal.