The initial solution would involve a website where you can connect your personal and work calendars (Google/Outlook) and then setup syncs between different calendars. Then it would synchronize all events from a calendar to another while making those events private. It also would synchronize new events as they come up and delete events that were deleted from the original calendar.
I'm currently trying to guage how much of a problem this is in people's lives, as such I'd greatly appreciate your input on a brief survey. Thank you for your time and valuable feedback!