When a decedent enters into a contract prior to his death, and it settles after his death, there is no step-up in basis. It is considered income in respect of a decedent. In such a case, the old basis is used and decedent’s estate or heirs pay the capital gains tax.
What are some of the solutions? 1. The Buyer defaults on the contract, the decedent’s family keeps the deposit, and a new contract is entered into. In such a case, the old contract is dead and a new contract with a stepped up basis is done. And to make matters worse, the contract is an assets of the estate and will bear estate taxes (if decedent’s estate is worth more than the exemption equivalent for estate taxes). So, this is a huge problem.

Let’s say, family enters into a binding contract whereby they sell a portion of decedent’s closely held corporation prior to his death to New and give New an option to purchase the rest after the death of the decedent. This would cause income in respect of a decedent and if Decedent was over the exemption equivalent there would be an estate tax as well.