Use Outlook Google Calendar Sync (OGCS) and sync multiple Google Calendars to Outlook

Download a portable installation of Outlook Google Calendar Sync. The software is free, but if you get it to work, tip the man a pint or two!
I have an Outlook calendar for work, and two read-only links from Google for personal and family. The issue is Outlook will only show free/busy schedule for the main calendar. So, if you have a doctor’s appointment on your personal sub-calendar in Outlook, your free/busy information is not show in Scheduling Assistant that handles your free/busy information. The entry has to be in the main calendar. It’s been like this since Outlook 97 and it has been a frustration of mine for 20 years. Anyway, my decision to sync using three portables instances allows:
  1. me to share family calendar with spouse
  2. all inbound to Outlook are private, so even if I permission to my calendar (see calendar title), personal and family entries remain private
  3. all outbound to Google is just work items
Type Sync Direction Color
Personal Google -> Outlook Green
Family Google -> Outlook Pink
Work Outlook -> Google Blue
Work: Warning: This assumes you don’t use Categories except for OGCS. I checked on <No category assigned> because I make an assumption that are all my Work calendar items and anything with categories is either Personal or Family.
You need to create a new Work calendar on Google:
Take care that you select Outlook -> Google otherwise you will be in a whole lotta trouble.
  • Sync a very small date range like 3 days past and future. You can fix issues without having to deal with 30 days of bad entries.
  • On Android & iOS, creating a new work entry requires one more step where you select the work calendar as opposed to Google’s work calendar since that won’t be saved during a sync
  • Worried about syncing reminders as I might get pinged too often from different devices