Can't sync SharePoint Calendar in Edit Mode

Hi All. 

I am building a SharePoint site for my golf club.  I want a calendar so I can assign tasks to people, such as Mow Greens, Mow Fairways, on particular dates, etc.  My objective is to have a calendar view online while doing the editing locally on my PC.  The reason I want this is it is much faster to add and move entries in Outlook than it is to do it online via the browser.  

I can successfully sync the calendar to Outlook, but it is always in read mode.  I want it to be in edit mode so I can make changes locally and sync them back.  I have looked under internet calendar settings in Account Settings in Outlook, but can't change it to read mode.  I have tried 2 approaches.  Using a Group Calendar and also using one of the legacy App calendars.  

One possible complication is that the SharePoint site is in Tenant A where as my primary account in Outlook is Tenant B. I do have an account for Tenant A set up in Outlook, too.

Questions

1. Any suggestions on how I can get a SharePoint calendar syncing to Outlook in edit mode?

2. Any suggestions on alternative ways to solve my underlying problem

  A.  I want tasks assigned to people visible online in an easy to follow format

  B.  I want to be able to easily assign, move, remove these tasks at a rapid speed.

Thanks for reading