I have been doing active development in C# for several years now.  I primarily build enterprise application and in house frameworks on the .NET stack.
I've never had the need to use any other mainstream high level languages besides C# for my tasks, since .NET is the standard platform we use.
There are some legacy Python applications that I have been asked to support going forward, I have no exposure to python and dynamic languages in general(although I've done a fair bit of JavaScript).
I was hoping to get some guidance/advise to aid in how to go about learning a language like python for the statically typed mind.
EDIT: Using IronPython is not an option!
You're going to experience quite a bit of culture-shock going from C# to the wild duck-typed outback of Python. Lack of types and intellisense can be pretty daunting. Good thing that you're experienced in JavaScript. Also know that indent-sensitive block rules of Python can be very confusing for the inexperience (usually you either love it or hate it :-)
Apart from that the biggest challenge moving from one language to another is usually the framework. Getting to know all the classes and functions Just Takes Time unfortunately.
Learning Python for a .NET developer