Rolling software is better achieved with better backwards compatibility than it is with constantly breaking API changes.
When you have constantly breaking API changes, and then someone has an essential plugin that's unmaintained, then they're a lot more likely to stay with your old, buggy, insecure base package, rather than finding someone who knows how to update their plugin (remember, most users aren't programmers, and most have installed plugins for a reason).
What you do is try to minimize the API surface that plugins have so it's easy to maintain backwards compatibility, and minimize the impact that older plugins can have by keeping them reasonably well isolated.
When you have constantly breaking API changes, and then someone has an essential plugin that's unmaintained, then they're a lot more likely to stay with your old, buggy, insecure base package, rather than finding someone who knows how to update their plugin (remember, most users aren't programmers, and most have installed plugins for a reason).
What you do is try to minimize the API surface that plugins have so it's easy to maintain backwards compatibility, and minimize the impact that older plugins can have by keeping them reasonably well isolated.