First, those stocks he owns are presumably highly appreciated compared to what he paid for them. Therefore, they will be inherited by his heirs at a stepped-up basis. Ie, the heirs cost basis will be the market value on his date of death. Therefore, substantial income taxes will be forgiven. He should therefore not sell them if he can avoid it.Otherwise, he will pay income taxes only at capital gains rates on what he sells. So sell them over a series of years to minimize income taxes--presumably as he needs the money.To save commissions use a discount broker.There are also trusts that could pay him taxable income from the trust and then transfer income or ownership to his heirs, but these may not be worthwhile unless his total estate including real estate, 401K, life insurance, and IRA exceeds $675K, the Federal Estate Tax Exclusion.
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