Ah, I think I understand now what you mean and at the same time I am wondering whether you are perhaps mixing URL structure creation, physical directory on the server and 301 redirects.
They are all three independent of each other!
I believe you have some kind of CMS and therefore you are probably not referring to a physical directory on the server. So I will concentrate on meanings of URL structure and 301 page to page redirects as I think you and your IT may be speaking "different languages" right now.
This post is long because of example given, sorry about this, but this was the best way I could think to explain (if I myself understood you correctly).
On the new site, since your pages will change URL anyway (because of the change in domain name part), you can create URL structure with folders the way you wish. Then you have to map the URLs from the old site to a new site.
The best is to explain with an example:
THE OLD SITE:
article1: http:
//www.myOLDsite.com/story/title1/date1
article2: http:
//www.myOLDsite.com/story/title2/date1
article3: http:
//www.myOLDsite.com/story/title3/date2
article4: http:
//www.myOLDsite.com/story/title4/date2
a) THE NEW SITE COULD BE (everything the same apart from the domain name):
article1: http:
//www.myNEWsite.com/story/title1/date1
article2: http:
//www.myNEWsite.com/story/title2/date1
article3: http:
//www.myNEWsite.com/story/title3/date2
article4: http:
//www.myNEWsite.com/story/title4/date2
b) OR IT COULD BE (similar structure as per old domain, only the folder "story" is now named "article"):
article1: http:
//www.myNEWsite.com/article/title1/date1
article2: http:
//www.myNEWsite.com/article/title2/date1
article3: http:
//www.myNEWsite.com/article/title3/date2
article4: http:
//www.myNEWsite.com/article/title4/date2
c) OR IT COULD BE (you split the "story" folder into two new folders and all articles go to one or another):
article1: http:
//www.myNEWsite.com/foreign-story/title1/date1
article2: http:
//www.myNEWsite.com/domestic-story/title2/date1
article3: http:
//www.myNEWsite.com/domestic-story/title3/date2
article4: http:
//www.myNEWsite.com/foreign-story/title4/date2
d) OR IT COULD BE (you insert a new subfolder after the story folder, and articles go to one or another subfolder):
article1: http:
//www.myNEWsite.com/story/foreign/title1/date1
article2: http:
//www.myNEWsite.com/story/domestic/title2/date1
article3: http:
//www.myNEWsite.com/story/domestic/title3/date2
article4: http:
//www.myNEWsite.com/story/foreign/title4/date2
e) OR IT COULD BE (you design completely different structure, no particular rules, for whatever reason):
article1: http:
//www.myNEWsite.com/anything-here/another-folder/title1/date1
article2: http:
//www.myNEWsite.com/title2/date1
article3: http:
//www.myNEWsite.com/story/domestic/title3/date2
article4: http:
//www.myNEWsite.com/title4/date2
The above is deciding on URL construct structure. Ideally, the construct would:
a) make sense to visitors
b) allow you to write simple 301 redirect rules in your .htaccess (means just less work)
In the above cases, for a) and b) the redirect rules can be easily written as there is recognisable pattern.
Cases c) d) and e) would require more complex redirect rules in .htaccess or it is possible that cannot even be done via .htaccess but instead you would need database mapping with the reference of "old URL" and "new URL" and redirect done by server script instead, after checking old/new URL pair.
Page to page redirect would mean that
regardless of the new URL structure you choose to implement your old URL of article1 would redirect to a new URL of article1.
In this case you will not have Soft 404 So if your IT director wants to preserve URL structure AFTER the domain name between two sites - this is fine, you will still have 1 to 1 301 redirects if you redirect old URL of article1 to new URL of article1, old URL of article2 to old URL of article2 and so on.
In fact, unless there is something seriously wrong with the current URL structure, or would create a mess in URL structure when merging sites, then for me this would be a preferred way to go.
However, if, because of merging sites, if you "inherit" the old URL structure makes the new site's URL structure looking mess (because of how existing URL structure looks at the moment), then you could revisit and decide how your URL construct will look like. As I said, creating (mapping) redirects for these will be much longer job as you would firstly have to create a spreadsheet mapping old to new and then implement this programatically (whilst if you are inheriting URL structure from the old domain, the 301 page to page redirect is a few lines in .htaccess).
<added>
If I have misunderstood your question and the post above does not answer it, then help us by giving the following example:
- pick up three (exemplified) URLs from your OLD site
- tell us where you think the redirect should go to (examplified target URL(s) on a NEW site for each URL from OLD site)
- tell us what your IT Director says such URLs should go (examplified target URL(s) on a NEW site for each URL from OLD site)
</added>
