In reply to David.

jetpack is one plugin that’s hard to debug locally.
I actually give up to test jetpack before updating (I test all updates before push them to live site for WP and other plugins).
I’m sure a lot of dev do the same because the way jetpack is built (as a Frankenstein monster).

@David Instead of testing locally, I'd suggest testing on a live sandbox, or a staging environment. If your testing environment can make and receive XML-RPC requests, it becomes easier to play with Jetpack and run all the tests you want! :)