Then the place to discuss that is in the political arena.
Violating regulations because you think the regulations stink, the regulators are wrong, they shouldn't apply to you, whatever, is wrong.
We probably all agree here that dumping mad pollution into the air is a bad thing, and that regulation should be obeyed, but all it takes is one factory owner deciding that that regulation sucks, and the air's unbreathable again.
Yes, the place to discuss it is in the political arena but whether you can change it in any significant way without the expense of significant resources is questionable.
There are many regulations that serve effectively to support a monopoly / oligopoly by installing market entry barriers (Taxi, TelCo, founding a bank).
Price controls effectively are regulations that can influence the well-being and survival of many people and in the years after WW2 the Germans were practically forced to break the regulations (against Reich and Allied law) in order to survive. You think they did wrong?
I also think that you (and everyone) should try to follow the laws (laws = regulations and much more) as much as possible as long as you do not believe they are unacceptably unjust. The dilemma between justice and law is itself a recognized part of law philosophy https://en.wikipedia.org/wiki/Radbruch_formula
I fully agree with your last sentence but even here I must ask what regulation is good for if people don't or cannot abide or it's not enforceable?
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.
And since all laws aren't good, people who break laws should not have to ever go to jail. Just fine them instead, regardless of the law, because some laws are bad.
But these days there are people who'd disagree with that assumption.