In 1Password's case, I understand their desire to switch over to subscription pricing, and also have some sympathy with the notion that moving people to a cloud

In 1Password's case, I understand their desire to switch over to subscription pricing, and also have some sympathy with the notion that moving people to a cloud-based model reduces confusion and complexity (including their support costs). I also have no doubt that they now intend to take security as seriously in the future as they have in the past. Beyond the not-insignificant risks of them screwing up, despite the best of intentions, there's nothing that prevents a change of company direction/priorities that could greatly increase the risk of a significant security breach. New senior people get brought in, crises happen that lead to poor decisions for financial or other reasons, and companies get sold to people who may well have completely different priorities.