Regarding automatic tracking tho, the easiest option is Bluetooth based, the app knows the identity of the car, when the phone connects, it knows you're probably starting a trip. And the same goes for connected car APIs, those can much easier take the place of an OBD-II reader.
a doable solo project, depending on whether existing cheapo OBD2 readers have good coverage of ECU data. if anyone sees this and has a point to make, please do let us know, otherwise this a donation to the noosphere that i will look into eventually if the feasibility/target market presents. the OP should also consider looking into this if he wants to be a sick cunt for his family (more than he already has been) - he would need a hot glue gun, and to know C (for ESP-IDF), Java (for Android), SQL (for database), and HTML/CSS/JS (for web). web is the champion use case of large language models, so this one section can be vibe coded, otherwise LLMs should only be used to learn how each function works as the system gets broken down into individual submodules.