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Read the divorce decree. Not to your question but just curious, who's been deducting the mortgage interest?

In general lenders don't rewrite terms because of transactions like divorce or contributing encumbered property to an LLC. Are you sure it wasn't handled through the divorce with an assumption of the mortgage by one and release of liability of the other? The other way would have been to refinance in only the one name.

"Probably a lot more to this story." The temp officer (at least in action) employee was naive (at best). Their testimony was 100% incriminating, tough to believe they even had representation. Oddly, I often get flamed when I point out how anyone who is part of the payroll process needs protection from this very issue. Even those who have no signatory power/responsibility. A payroll keypuncher who could have seen no withheld items were ever paid, those who login only to make deposits, etc., can all be named in a suit, and at best will have to pay to defend. I carry insurance for frivolous suits, even though I am not liable at all, defense is expensive. I bet all here do the same.

If he doesn't have his Vanguard stmts for each year, V should be able to supply him copies. He can also get the information from his IRS transcripts of form 5498 and figure it out from that.

A fair chance there was insignificant taxable profit, which is the only part which may be taxable. Remember, the contributions are not double taxed, they were taxed when earned, so they can be withdrawn at any time.

This reminds of an interview with some prospective clients who wanted to deduct their Million $ Motor Home as a business expense. The IRS position will be that all second home expenses are personal. Your clients will have to document all of their business related deductions.

Business mileage on the island would be a biz deduction, not all mileage. Be careful about mileage that tries to turn personal mileage into business mileage. Does their mileage log support their biz miles? Ask lots of questions.

Exactly!

For 2023, the widow can't file as QSS because the TP died during that year. Her choices for 2023 are MFS or MFJ, but joint is only available with permission from executor of his estate. I would suggest she continue as MFS so not to open up the possibility of her becoming liable for his tax debts. QSS is available to a widow that meets the requirements in the two tax years subsequent to TP's year of death: 2024 & 2025. I have never dealt with CNC status and do not know if that would remove the protection from TP's tax debts that MFS has afforded her since he is now deceased. His tax debt would become a debt of his estate, and any assets should be used to satisfy that debt before she gets anything.