Re: UPDATE
Play with a $10-$20 CAP so that players cannot lose more then a set amount in 1 hand, or allow ratholing in your game and encourage this player and any others you feel sorry for to do it.
Anykind of limitations on how deep the game is will help this player's chances. Heck, even bumping up the blinds and playing with the same amount of money or adding more blind money to the game through straddles, etc... would help him out.
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