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I've recently been researching the structured settlement (annuity) industry. It seems like as soon as someone has a guaranteed set of future payments, you will get structured settlement brokers reaching out, offering to buy out their future payments for a (often low-ball) lump sum today, and many will take it. Will you permit these kinds of side deals?

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You can't sell your social security benefits, so I would guess the same restrictions would apply.

You can - by taking a loan.

Right, often the guarantee of future payments can be treated as collateral to make getting a loan much easier. At a minimum it can be used to show proof of future income.

I assume this would be resolved by making BI payments immune from bankruptcy.

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