Dear CTLawyer,
I live in Israel, and so my answers may not apply to you, but if you were here, these would be the answers:
1. Do I tell my son and daughter in law about this call?
A: Absolutely. They may already know about it, but are waiting for you to mention it.
2. Is this an indication that the prospective in laws expect grandparents to support married children and grandchildren?
A: Yes. Grandpa has money and it’s only right that he share it . Family is family, no? Do you think the mechutanim have not heard about your Connecticut estate?
3. Was the prospective grand father in law out of line in making the request?
A: As out of line as can be. I call it chutzpah.
4. Is this a new custom or a custom in communities in which I don’t live?
A: It is a new custom. You are the first generation (statistically, not you personally) to have made it in America. The previous generation were immigrants and survivors, and didn’t have the means. It’s a new age.
5. If I pay for this am I expected to do the same for all my other grandchildren?
A: Big time. As an experienced attorney, you are familiar with the term “precedent”. If you pay, you’ve set one.
Good luck