Depends entirely on the effect of the regulations. You could describe the divisive racism laws of the past in USA as regulations, wouldn't it be better to break them anyway? Do no harm, law or not.
Still, if you break a law, you should face consequences, whether you're doing right or wrong. That's the point of civil disobedience - willing to accept the punishment for going with your conscience.
Then there's a difference between breaking the law out for moral reasons and breaking them because they're inconvenient and you could profit more by ignoring them.
And for each of your scenarios I can invent two in which your actions are just parasitic, in which you freeload on your community. It's easier to make a profit when you don't play by the same rules as everyone else. Also, if you run a startup, you're likely not struggling to feed your kids, so the moral picture you're painting does not apply.
Then there's a difference between breaking the law out for moral reasons and breaking them because they're inconvenient and you could profit more by ignoring them.