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)
I recently decided to start tracking my life todos in addition to the work projects, which was as simple as creating a life directory and running `git init`.
Org-mode does require using emacs, if it is too crufty for you or you don't like the learning curve, try spacemacs! Its org layer is well configured, and it is also well suited for modal editing if that's your thing.
For long term goals and planning, I prefer to break things down into bullet points, and categories, and check them off as I go. https://taskade.com has been great for that (though no calendar integration), especially with their Chrome Extension that loads your most recent list on each new tab.
Todoist is replacing Wunderlist for me with their more frequent updates.
The "Apple-ification" as you put it is done pretty well. In place of drag + drop to set a time of day, tasks can be created with inline date parsing. So tasks can be created with something like: "Meeting with Tim at Tues 3pm", and it'd pick that up. It's missing direct support for habits aside from having recurring todos.
If you'd like, I've got a 3-month premium code left over I can send your way. Not affiliated with them, just a happy user.
I too have tried most if not all of the tools in @renaudg's post and have come to the same conclusion: nothing really matches Timeful.
Yes, WeekPlan allows for todos, repeating tasks and appointments to live together.
Additionally, you can set goals for each of your roles in your life (father, colleague, brother, etc...).
It doesn't help tackle longer term goals yet though, for that you could check OKR softwares.
The one thing it might lack is guidance to organizing projects/subtasks/dependencies. But luckily I don't need those in my calendar.
moo.do just added that as a new feature. I've not logged back in to try it again but it might be worth having a look at?