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Very insightful.

FYI: Keeping that 2nd check would be insurance fraud.

Regarding fees: S&P 500 index fund. There has yet to be a fund manager who can CONSISTENTLY outperform the index over the long term. But they'll all charge you for failing to do so. Also, dollar-cost averaging is your friend. Assuming your horizon is 20+ years out, set it and forget it...

Love it or leave it, eh?  Yuck.  We can (and must) do better. The fallacy in comparing what your SS contributions would amount to with what SS will actually pays you is that that would have left multiple generations completely in the cold while your money built up.  Great for you, not so great...