I did just this type of thing a little over a year ago and organic traffic is up over 300% now. We made the change mainly to improve the structure of the website(s), with more logical organization and better internal linking. We did do the move all at once (thousands of pages) but it took a lot of behind-the scenes planning to be ready for that.
First came the decisions about what sections and categories made sense for our site. (Using the URL structure to guide users around the site makes it easier for them to find what they are looking for and interlinking between related posts as appropriate is also good—and this helps a lot with search engines.)
Then came the organization of posts into their new categories. To make things easier, we kept the individual path names the same (so www.siteA.com/old-category/old-post-string became www.siteC.com/new category/old-post-string) and uploaded them into their new categories when the time came.
We also used this time to do a limited content review (posts with the most traffic) and we updated a lot of these. We made the choice to keep most of our old posts, even though in our market they can get outdated quickly, to conserve any links we may have acquired. (The main site that we were directing to the new site was pretty old and had picked up a lot of links over time.)
We could have done a more complete content review before the changeover, but in part we wanted to see how these posts did under the new structure—we did get renewed life out of some of them, and we further updated and optimized those.
In conjunction with the export of the old sites to the new one, we made sure to 301 redirect all of the old posts to their counterparts on the new site. For the posts we chose not to bring over, we 301 redirected them to a related post in the same category.
We still occasionally come across things that need to be fixed—old posts that need redirecting/updating or 404 errors that need to be tracked down (one big issue we found was a lot of old pages had old links with hard paths to the old website root domains, causing a bunch of nasty internal not found errors—not good!) but overall we are happy with the change. (Up 308%!)