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I try to ask some general questions about ownership, spouse ownership, about services and relationships to other businesses, about employees paid via a staffing company, and such. Keep them simple and non-technical. If any of these questions gets a positive response, the next step is a phone call. Just too many variables to reduce to a checklist. And even if it were reduced to a checklist, it would be too extensive and clients' eyes would glaze over.

If the worker can find or borrow enough money to pay the initial payment the landlord calls for, might she fail to pay rent until the landlord delivers an or-else eviction notice? Would that set up a recognized need for “[p]ayments necessary to prevent the eviction of the employee from the employee’s principal residence”? I do not recommend this. Rather, it illustrates one of the many absurdities in this bit of tax law.

Yes.

Yes

Not enough detail.

Thanks, Brian! Love your office hours!

However, there are bigger issues to worry about here--including: Issue #1: Medicare Will Pay Primary (COBRA Coverage Can Assume Primary Medicare Payment Even If Not Enrolled) Issue #2: The Eight-Month Medicare Special Enrollment Period is Not Extended by COBRA Enrollment Issue #3: COBRA Does Not Qualify to Avoid Part B Late Enrollment Penalties Full details: https://www.theabdteam.com/blog/how-cobra-and-medicare-interact-for-retirees/ ABD Office Hours Webinar: Medicare for Employers (see slides 12-16 in particular)

Update: The Grumman Pension was separated as per the QDRO! There was a hold-up because of co-ordination and communication issues between the previous plan administrator State Street and the current Fidelity. This site is an amazing resource. Thank you for your sharing of your time & expertise.

Update: The deceased DID have a son. I found him by sending out a letter to an elderly relative I found on Truthfinder.com. She turned out to live next door to the kid, and he called in with all of his information. We do at least have someone to pay! And yes, I did ask him for a birth certificate so I can prove to myself that he really is the son.