I have not found a good calendar sync, but this is how I manage my calendar to my logins. I do copy incase one is inaccessible or locked out I can always go to a Backup. I do this on a semimonthly basis, this way I don't lose birthdays or PTO.
mac calendar export (file->export)
outlook import(add calendar-> from file) , export ***must use the share (CAN DISABLE WHEN DONE TO MAKE IT PRIVATE AGAIN) eg to gmail -import (then use gmail to export)
gmail import (settings>calendar> import)-> gmail export( settings calendar >export)->
yahoo import(select my calendar ->import) , yahoo export (my calendar->export) ->
mac calendar import (file->import)
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