What is required is frank conversation with the stakeholder/customer, because there are so many trade offs decision to make. Devs don’t like to estimate tasks because there’s an exploration phase (which cost time an energy) to have the solution and the cost of time and energy for the implementation. And it’s recursive. Agile was basically saying, let the devs do their thing, but have a conversation every once in a while to discuss new directions to the projects based on new evidence found. And unless the team have already built the same project (with the same people involved), it will always be a bet. No amount of tracking or insight will remedy that.
Agile recognizes that software development is a design process with uncertainties and not a repeated tested manufacturing process (product development versus product manufacturing). With the uncertainty of a design process in mind, and the need for estimates, it suggests comparing similar tasks to get an empirical estimate. But since it's just an estimate, you regularly need to validate that the estimate is still considered correct.
