I don’t have any experience with tools that do it automatically (swig?) but I wouldn’t be surprised if they existed for python too. My approach has been to expose whatever I need to expose by hand. OMPL I believe generates all the bindings automatically so that could be a thing to look at.
I know Nate really likes Ruby, but I’ve always felt it was a weird choice since I’ve never heard of it used for anything in robotics. Do you know of anyone outside of open robotics using the Ruby bindings or expressing interest in them?