In my opinion, part of the issue with Jetpack is their UI. They have done a poor job in making the paid features discoverable.

They have recognized the lack of conversion of free to paid accounts and have attempted to solve the issue on the backs of the community rather than revamping their own product's UI to do a better job of demonstrating value.

The idea of Automattic owned products getting a pass is dangerous. Great comments by JJJ on this topic.