Dan Evans, Plan9
"I've been using your bulk manager all morning deleting 1000s of pages, members and media files - it's been a life saver."
We've just released V1.10.4 of SEOChecker. Normally we don't write a news article about a bugfix release but this one is different. This release should be called the "failed assumption fix release"
A few months ago we've released v1.10 with a complete new repository that increased performance with a few 100% on large sites. The reason why performance improved was that we dropped our UrlHistory tracker functionality that was kind of black magic under the hood. It tried to fix a url based on url parts. This was mainly because we didn't like the idea that on every node change all kinds of redirects were made like the Url Tracker did and the new Umbraco Redirect tracker does. We kept those url parts in a History table and only when a 404 was raised we tried to create redirect based on this history. Worked very well on small sites and the redirect overview was never filled with url's that will never be requested.
Then we got the idea to use the Redirect functionality of Umbraco that stores the url changes and check that table for our 404 handler. After a few support tickets we came to the conclusion this didn't work as well either because it was confusing that when the redirect manager in Umbraco is not used it still had the function to store url changes.
Well I think you can guess what the current solution is. When a url changes it will create redirects for the page and all underlying pages directly in the redirect manager. As a bonus this will work also for media items. And a nice feature that comes with our redirect manager is it displays how many times and last time a redirect is accessed. So if a redirect is never accessed you can delete it from the overview.
Don't try to be smart. It's better to have transparent solution everyone understands than to build a system that confuses people.
Hope this version will fix your issues and sorry if you ran into issues with url changes last few months.