I was looking for something to solve your delimma on the Mac App Store and ran across Cardhop, an enhancement to Contacts that might, give you at least some of what I think you are wanting and works in macOS, iOS, and iPadOS. It will NOT free you from the necessity of having separate Contact entries for each person in a family or company, as it is based on the Contacts database and its connections to Mail, Messages, Facetime, etc., but it does add "relationship" tracking between contacts. Not only the relationship but what the individual is in the relationship. That permits you to identify Sue Jones as the company president, Bill Smith is their sales representative, and Jim Wallace as Sue Jones "Significant Other" or truthfully whatever relationship you can think of, and provides transportation from any individual in a relationship to all of the others. Even better, any individual may be in multiple relationships, so Sue Jones can be in a company relationship, and a family relationship.

Cross device synchronization is subscription based service, but the subscription also includes the highly regarded Fantastical in the same subscription, and there is a free two week trial. I don't know if either of these would work for you, but I thought I would pass them along for what it is worth.

DISCLOSURE STATEMENT:

I have no relationship, pecuniary or otherwise, with Flexibits, the developer of Cardhop and Fantastical, other than that of a subscriber.


If we knew what it was we were doing, it wouldn't be called research, would it?

— Albert Einstein