Ok, so I've narrowed down the issue and am able to resolve this (manually, will check out automatic but likely may not, we'll see what time says).
So, this was an imported project from Sitefinity 3.7 to 6.3.5000. Many pages in the backend views, SHOW that the setting for the page is 'Site default caching' profile. BUT when you check the pageData properties for a page, page.pageData.OutputCacheProfile appears as 'NULL'. Which under my current checks, is what SHOULD dictate if the page is being cached and under what property.
Fix,... go to page -> edit page -> edit 'title & properties'. Don't change ANY settings, hit save (returns to page content edit), hit save/publish (returns to page list), then run the check again, and this time instead of a null, profile is "" or string.empty therefore now the page is reported properly.
Hope this sounds good, could just be a migration issue.