To further clarify, I believe his opinion was that it would take a long time to create a 301 redirect from one URL to another URL (page level - which is what I proposed and what I believe you are proposing as well) and it would be easier to 301 a directory URL and all of its contents to another.
So instead of doing this:
Redirect 301 /title1.html www.newdomain.com/title1.html
he wants to do this:
RedirectMatch 301 ^/story/ www.newdomain.com/story/
I should also mention that the domain we are merging into already has a /story/ folder.