The uncomfortable parts, said plainly.

Usually not on its own. Internal Revenue Code §2703 directs that property be valued without regard to the agreement unless it meets three statutory requirements — and clearing them is only half the test, because courts read §2703 alongside an older regulation, and the case law reading that regulation demands a price that is fixed or determinable and binding throughout life and death.

A unanimous Supreme Court says the proceeds count, and the company’s obligation to buy the shares back does not cancel them out. The insurance bought to fund the redemption enlarged the value of the shares it redeemed — decided on summary judgment, on a record in which nothing about the rest of the company was in dispute.

Yes. The objection most people expect — that the family still controls the company after the gift — was abandoned by the Internal Revenue Service in Rev. Rul. 93-12, which revoked the ruling that had made it. What stays contestable is the size of the discount, the restrictions relied on to support it, and whether the return disclosed enough to start the limitations period running.

It depends on the forum, and the disagreement is not at the margins: the reputational value of a sole practitioner's practice that New Jersey distributes as property, Texas holds is not property in the marital estate at all. Whether goodwill is divisible is a characterisation question answered by state law before an appraiser opens a spreadsheet.

Appraisal is an exit a corporate action triggers, and no wrongdoing need be pleaded or proved. An oppression buyout exists only because misconduct is alleged, the election to buy usually belongs to the other side, Texas has no buyout remedy at all, and the words "fair value" do not carry the same instruction in the two statutes.

Sometimes, and it is answered as a question of law by the forum rather than by the appraisal. Two different discounts are in play, they do not travel together, and a state can bar one while permitting the other — while in Texas the prior question is whether a court-ordered buyout exists at all.

Not the appraiser. The proceeding fixes it, sometimes in the statute's own words and sometimes by handing the choice to the trial judge, and the difference between those two regimes is worth knowing before anything is filed.

No. And the question that decides more matters comes first: whether the proceeding permits a marketability discount at all. That is fixed by the governing statute and the law of the forum rather than by the appraiser, and in the states that have enacted the Model Business Corporation Act's appraisal definition the statute answers it on the face of the text.

Fair market value is one definition, supplied by regulation and carried in the same words through the authorities that use it. Fair value is a label whose content is supplied separately by whichever statute, court or contract imposed it — which is why, in a dispute, the first question is not what the business is worth but which definition the law has already chosen, and that question is argued as law.