If he is on medicaid then he isn't "living" on 432/month. That would be living on 432/month PLUS whatever medicaid is worth, likely well north of another 500/month.
Then the kids need schooling, either in-person or remote. that is another 10k/year/kid. And you need some sort of local police/justice system to ensure nobody boots you off your homestead. But even once you account for all those local costs, there are things like national security. Living a peaceful life on a remote farm is only possible because the country is ringed by police and armed forces. Those things may be a thousand miles away, but someone still has to pay for them.
The problem with regulation isn’t that there are never any positive effects, of course there are.
The problem is it’s impossible to reliably avoid adding substantial friction to life via overly broad regulation that is not applicable but has to be followed anyway, or outdated but still-in-effect regulation that is not applicable but has to be followed anyway, at least.
If this only bothered huge companies then I would say cost of doing business, who cares, etc, but it actually affects things like how cities and towns are designed, how expensive housing is, how expensive medical treatment is, etc.