Given the downsides though, its worth writing the little bit of code necessary to convert your objects to a JSON-able form if your code is ever going to be used by people other than yourself.

Disagree strongly. You have no idea how complex my graphs of (pretty damn complex) python objects are and how much I value being able to change their organization without having to rewrite the serialization code every time I do so.

Don't fear pickle. Just don't expect it to be secure or amazingly fast.