Is there any reason fans can’t crowdfund insurance policies for returning seniors?

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I know this wouldn’t work, but why wouldn’t it?

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Because the NCAA

I’m not spending money on a college player to return.

An insurable interest is required for insurance. The fans don't have one and cannot purchase it themselves. Therefore the policy would have to be purchased by the player or for the player. This is the same as giving the player the money to go buy an insurance policy. Thus, this is the same as giving a player money.

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An insurable interest is required for insurance.

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The fans wouldn't be the beneficiary of the policy.

it would be considered 'compensation'

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An insurable interest is required for insurance. The fans don't have one and cannot purchase it themselves. Therefore the policy would have to be purchased by the player or for the player. This is the same as giving the player the money to go buy an insurance policy. Thus, this is the same as giving a player money.

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This is incorrect. As a lawyer, I see some third party beneficiary contracts similar to these, but they are indeed rare

Other than an illegal extra benefit paid by boosters (which you would automatically be when you provide a benefit) that would trigger SEC and NCAA penalties and maybe even an NCAA investigation of your school I don't see a problem.

That’s pretty interesting. I hear it’s a mess and very hard to get the insurance company to pay claims.

I'm pretty sure the player doesn't actually have to pay for the policy till his college career is over anyway, so they can pay for it with money off of his first contract/endorsement deal