There is an expression in legal fields that "pigs get fat and hogs get slaughtered." I, too, have heard of people taking 50% valuation discounts. I think that is an aggressive posture and you might be asking for an audit. You have a fairly complex arrangement, here, and it does not make sense to do this without consulting a tax attorney to make sure that you handle everything correctly.
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You should have an appraisal done for both the value and the discounting. I often recommend having the appraisal done every other December so that you can use it December and January.
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