I think you're making this out to be more complex than it really is.
Deemed disposition technically occurs at the moment before death, before assets are transferred to the estate.
An executor who hires a tax accountant who doesn't inform them of the deemed disposition rules, doesn't question them as to why there is dividend income with no corresponding deemed sale and who doesn't describe the clearance certificate process hasn't received very good service. Not trying to throw anyone under the bus, and I don't even know if the poster hired a tax accountant.
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