A personalized assistance system for a user of a vision correction device includes a remote computing unit with a controller having a processor and tangible, non-transitory memory on which instructions are recorded. The controller is configured to selectively execute one or more machine learning models. A user device is operable by the user and includes an electronic diary module configured to prompt the user to answer one or more preselected questions at specific intervals. The electronic diary module is configured to store respective answers, entered by the user in response to the one or more preselected questions, as self-reported data. The controller is configured to obtain the self-reported data from the electronic diary module and generate an analysis of the self-reported data, via the one or more machine learning models. The controller is configured to assist the user based in part on the analysis.