(In reference to “The future of dynamic languages is less than crystal clear”), the pop in Python’s popularity seems mostly due to the short time it was the only option on Google Apps. Now that a JVM is available in that environment, it appears to be dropping off.
The real key to productivity these days is how well everything integrates with an IDE. There’s just too many APIs out there to be flipping back to forms to manuals, so context documentation and object inspection is an essential. Dynamic typing doesn’t work well for this because you can’t determine type by the syntax.
Also, when dealing with a lot of developers working on a large application, an enforced structure becomes very important.