Alternatively, is there any other software with this feature? I have been looking for one for a while but no luck :-\
That (and scheduling suggestions) used to be the main feature of Timeful, an app started by behavioral psychologist Dan Ariely. It actually got acquired by Google and shut down. Sadly, Google Tasks still pales in comparison.
The only todo app I’ve found which allows you to do this and has desktop/mobile versions is TickTick. I used to be a fan of Things which is nearly perfect, but the authors stubbornly refuse to implement this, so I’m gradually migrating away from it.