I built bindings for various C++ libraries in SWIG (not only for Python but also Lua and Ruby) and I was always very impressed with the result. What's amazing about SWIG is its ability to easily port very complex and rich code. I successfully exported very complex class hierarchies and code relying heavily on pointers and STL to Python and/or Lua. The process consists of writing several header-like configuration files that SWIG ingests and uses to generate bindings, which is often pretty straightforward. Often you can simply import the normal C/C++ header files in those configs and add some glue code / extra hints to help SWIG in cases where it can't figure out what to do with a particular type.
In my experience, the most difficult aspect of binding generation is not writing the glue code, but doing so in a scalable way. Manually writing bindings for any real-world C++ codebase would therefore be extremely tedious (IMHO), so having an automated system that does this work for you is a huge time saver.
Some larger libraries / frameworks have their own wrapping generators Btw, PyQt (which provides extremely good bindings to QT) for example has SIP which is worth looking at (it's open source).
In my experience, the most difficult aspect of binding generation is not writing the glue code, but doing so in a scalable way. Manually writing bindings for any real-world C++ codebase would therefore be extremely tedious (IMHO), so having an automated system that does this work for you is a huge time saver.
Some larger libraries / frameworks have their own wrapping generators Btw, PyQt (which provides extremely good bindings to QT) for example has SIP which is worth looking at (it's open source).