dblock - 2:56 pm on Aug 30, 2013 (gmt 0)
@aakk9999 thanks for that detailed response, it is much appreciated! you pretty much nailed it. You are correct in that we do have a CMS and thus I am referring to the URL structure. I agree with you that options A and C will be the better options. Luckily for us, the two sites we are merging have a very similar URL structure so there is recognisable pattern, which makes the page to page redirect bearable.
I probably should not have used the word "directory" and rather should have referred to it as the folder (or sub folder) in the URL. Nevertheless, what you mentioned above is what I have proposed. Unfortunately right now the IT Director is out of the office until later today, but I definitely plan on sharing your posts with him. I believe what he was trying to say was this:
these are links from the old site:
and so on. If we took all of the stories in the /story/ folder (in this example title1, title2, and title3) and redirected based on the folder/category level, so the entire /story/ folder on the old domian would be redirected to the new one:
Thus moving the entire folder over to the new domain so you don't have to do it by story, but rather by folder. How would that affect all of the stories in the /story/ folder?
Nevertheless, I'm very thankful for your response above as you have given me the actual reason to represent my case.