This post is so helpful. Thanks to all that participated.

With respect to: "The 1099-R is simply about moving money to a person as a retirement benefit or from an account or annuity or other provision."

I have a situation where the taxpayer is retired from Anthem with full health benefits that extend to his family (wife & 2 kids). The wife has a Sch C law practice - only source of earned income now.

I seems that the "other provision" fits here. 

Only Anthem benefit the retiree is receiving right now is the health coverage which is not reported on a 1099-R per Anthem's website since it's not taxable. He said he also did not receive a W-2 either (I've seen Altria report it this way where Box 1 wages were $0). It is as if Anthem is reimbursing for the cost of the insurance.

Can you conclude that the taxpayer paid for the coverage to then claim as SEHI on law practice Sch C?