I don’t think your travel insurance will cover any delay because a connecting flight in the travel insurance world would be flights on one ticket, or one PNR, and you have two separate tickets. And air travel in the travel insurance world is not public transport, that is typically buses and trains, and taxis.

As others have said, major changes are possible to flight schedules on both flights creating a problem no matter what you book. If it were me and you would lose a substantial sum in the event of a misconnect, I would fly in the evening prior.