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any thoughts?
From my personal experience,
Use 301 redirection, use of robots.txt and the google URL removal system to remove all the old CF pages. I had a same problem while changing filenames and folders for a website, and it was solved by using robots.txt and Google URL removal system.
For 404 errors, you may redirect the users to your home page or a customized error page.
Use robots.txt as
User-agent: *
Disallow: /directoryname
Disallow: /dirrectoryname/filename.extension
Disallow: /dirrectoryname/filename.extension
and place it in the root directory.
(* would disallow all search engine spiders to crawl the above mentioned directories and filenames)
This way you may remove all the old pages within 3-5 days of using Google URL removal system and similary, other search engines would drop these pages in next crawl.