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409A valuations are almost always paid for by a party that has some interest in the outcome being high (or low). Moreover, said party usually decides who does the 409A valuation.

Valuations? You realize the valuation of a small company is much, much harder than the valuation of a public company right? I know a valuator who can take the information of a public company and tell you to about 10% its price on the stock market. 10% isn't good enough for playing the stock market, but with small companies the error factor is like 1000. Meaning your unicorn could actually be worth a million (firesale of assets, IP to patent trolls, fighting over scraps of the VC money) or a trillion (FAANG will now be referred to as FAANGU, U being for Unicorn corporation, your company). It might be more than 1000, it's really all over the map, I can say with certainty though it's less than 1000000.

My limited experience has been that 409a valuations are extremely different from what investors pay (what investors pay per share is much more). I am curious if there has been much written about why this is.

It mostly comes down to conflicts of interest.