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We still haven't cleard up which day he should use for the value calculations. When it goes in the mail? When it leaves his account?

The IRS told me last year that my holding period for a long term cap. gain began when I "controlled" the shares. And I bet this is the key word in this case as well. You probably control the shares right up to the instant they are transferred from your account, and then that would be the day to use.
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