I feel we think about this topic very similar.
My Outlook/iCloud calendar i only use for appointments, meetings and so
one. It would get very confusing if i would put tasks there. Sometimes i
use a different approach and drag calendar elements into MLO.
I absolutely agree with you about start
Here's how I would handle this:
I would leave "use time" turned off, so that the start date and start due
date do not show any time
Then I would set a reminder on the task set for 19:00 on start date.
I believe that whatever time you complete the task it will be regenerated
for x days hence, wi