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It is legal to have the condition on the death benefit, so he definitely doesn't need to remarry if he wants to keep the annuity.
However, you can certainly have an unofficial ceremony - you just can't apply for and get a marriage license.
No, it won't cause any trouble anywhere because you're not making any legal change to anything - you're still not going to be legally married.
You can have a power of attorney and living will for each other - that's no problem. There's no requirement for you to be married or related in any way to serve in that capacity.
You should be fine in doing all these things.