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...unless it was BRK-A =p).

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BRK is almost just another sort of mutual fund.

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It would be devastating if one of the companies I own went bankrupt... but it's hard for me to calculate the likelihood of this. One in a million?

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Give yourself a few more years and a few more investments and you'll get stomped by one. The company doesn't have to go bankrupt...there are probably twenty companies that drop to 1% of their former value and then get bought in a firesale and avoid bankruptcy for every company that actually drops to 0.

My sis-in-law years ago took her IRA money and basically handed it to a full-service stock broker. She didn't know any better. She told the guy "buy some Microsoft and buy some Starbucks and do whatever you think is best with the rest". So she got 10% into MSFT, 10% into SBUX, and 80% into Lucent. She made a little with MSFT, made a lot on SBUX, and lost 90% of her 80% on LU. (I told her ages ago she shoulda sued the bastards... no way in Hades a rational investment professional could possibly think 80% into Lucent was an appropriate retirement choice.) LU isn't bankrupt, but it fell to almost nothing before Alcatel bought 'em. Who coulda thunk a piece of the former-glory that was the pre-breakup AT&T could do this?

And how often do banks and S&L's and Credit Unions go bankrupt and have to be saved by FDIC and FSLIC and whatnot? What're the odds? Somehow I've had money in two of these. Fortunately, not >$100K or I woulda lost it. I mean, really, how could lightning strike twice?

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Would you rather get all in with AA vs AK for a $1200 pot, or get in with KK vs AK for a $300 pot, 4 times in a row?

Your expectation is higher with AA vs AK, but your likelihood of having SOME money left at the end is MUCH greater showing down KK four times.

Assuming my bankroll could handle the swings, I would much rather buy the one AA 'stock' than the 4 KK 'stocks'

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ok... so you're 70 years old, disabled, and living on $1200/mo of social security and $1M invested generating $5000/mo of retirement income. If someone offered you 50:50 odds on a coinflip for your entire retirement, would you accept it? 3:2 odds? 2:1? 3:1? 10:1? At what point is the chance of eating dogfood and having no way to pay for your prescriptions worth it?

Now roll the clock back and you're 22yo with $50K and 50 years of earnings potential ahead. Where would you draw the line? Different sorta question.

Which is why one size will never fit everyone. Diversify or concentrate? Buy&Hold or Buy&Homework? Individual stocks or ETFs/MutualFunds? Leverage or not? Daytrade or Blackjack?