I found an older thread (now closed) with the same question, so am resurrecting:
I am transitioning an org's homemade site in iWeb (blarg) to a new site I've built in WordPress. iWeb created a tangled mess of dozens of awkward nested URLs throughout the existing site. I am curious if there's been any further investigation to adding a wildcard character so a user could redirect all of the previous pages in a given /dir to the new page (or in some cases to the homepage) in one fell swoop.
After wrestling with another redirect plugin for the better part of a day, I was thrilled to find a recommendation to switch to Simple 301 Redirects -- straightforward and brilliant. A wildcard character option is the only item on my wishlist.