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My understanding is the 409A is supposed to be a true valuation of the company, not of the shares. The price of shares sold to investors (probably with liquidation preferences, extra voting rights, maybe a board seat, etc) of course costs more than the company's value divided by number of shares.

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409a includes the valuation of the stock held, which is often discounted by "accepted discount factors" such as illiquidity discount and marketability discount. The latter being the fact that a common shareholder often has resale restrictions on their stock.

It's both, they start by calculating enterprise value, then from there estimate the value of the common stock taking into account the things you mention - then divide that by number of shares (including those expected to be issued shortly).

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