I agree with a lot of this and you aren't even touching on some of my biggest fears, violating US employment and tax laws.
We are treating him like a contractor here but is he really a contractor based on the type and condition of his work? Is the DAO somehow going to start issuing 1099s? As the DAO is community owned, do we as SPS holders now have business expenses which will end up on tax returns.
I really don't want to go down this route of being an employer.