I have used PyGame for a while now, and quite enjoyed doing so, but only 2D experience is not going to cut it when I apply for video game jobs, and besides, I have a number of ideas I want to try out in 3D. What 3D library should I go into first? I was considering Irrlicht, which will also force me to work on my C++ again, but I was also looking towards XNA, as it would be cool to write 360 games. Any suggestions?
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In my opinion, going with Irrlicht or OGRE is a good idea. It will help you get back in touch with C++ and experiment with 3D without making it too easy. It is a good idea to learn XNA as well and build a few 3D game prototypes there.
Summary: Do both, eventually. Learn OpenGL/DirectX later.
All the best.