For this reason, I sorely miss the Timeful app (bought and shut down by Google) which nailed the process perfectly, integrating one-off todos, habits (e.g. 3 runs/week) and calendar management in a single system. AI-based suggestions for scheduling todos was the icing on the cake.
To this day, sadly I still haven't found a decent replacement.
Google Calendar took the automatic habits scheduling engine from it but is otherwise inadequate for todos, and well-established todo managers like Things / Wunderlist stubbornly refuse to allow something as simple as drag+dropping todos onto a calendar at a specific time of the day (which is the critical bit), and they don't support habits ("tick this box n times a week")
Plan (getplan.co) seemed promising but is too alpha for daily use and development seems to have stalled. SkedPal nails it in theory but is over-engineered and bloated, its UI asks too many questions and cognitive load is high, it needs "Apple-ification".
Any other recommendations very welcome ! Even happy to beta test or collaborate on something new (I know the world already has too many productivity apps, but it lost the "right" one with Timeful IMHO)