I've been building towards something like this with Conjure[0].
I've focused more on metrics, behavior, and achievement, with a rules engine for automatically completing habits and goals off those.
As you identified, the biggest obstacle for users has been the friction and overhead of tracking at scale. Integrations and automations have decreased that a lot. Transforming unstructured input through AI is super promising, and probably will make it more accessible to people who are less of the power-user/productivity-junkie persona type.
I've focused more on metrics, behavior, and achievement, with a rules engine for automatically completing habits and goals off those.
As you identified, the biggest obstacle for users has been the friction and overhead of tracking at scale. Integrations and automations have decreased that a lot. Transforming unstructured input through AI is super promising, and probably will make it more accessible to people who are less of the power-user/productivity-junkie persona type.
[0] https://conjure.so