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Lying, and not following the law, are both immoral without a sufficiently good reason. "I want to make money" isn't remotely good enough of a reason to lie and break the law.
‘Shit needs to get done and these kinds of adversarial boards aren’t doing what they’re supposed to’
That's closer. But if you think anyone circumventing the planning board process is actually doing it because they want to better society, and not because they want to profit, I have a bridge to sell you. A fine property in the middle of the Mojave desert.
What’s wrong with that? Circumventing the planning board is a good deed that deserves remuneration.
First, that is not a good deed. Fixing the regulations would be a good deed. Going around them is (somewhat) bad on its own merits.
Second, even if it were good, doing a good deed only carries merit if you're doing it for its own sake. Doing it to line your pockets means you don't have any moral credit for doing the good deed. And since this isn't a good deed to begin with, that means that we're now talking about doing a bad deed for selfish reasons, which compounds the badness.
An ideal, yes, but conditional on the possibility of the regulators letting you fix it.
I understand the content of the moral imperative here, but I think we need to look at the Soviet Union to understand where this falls flat. The system was built and sustained on lies, there were lies and deceptions and samizdat all the way down and it made for an awful society, but they had no choice. Things literally could not get done without people being deceived at various points in the Great Chain of their society.
There are no practical rules to live by here, other than "have an honest and fair system from Day 1" and "anything that lets you sleep with food in your stomach can't be that bad."
I would say that your scenario (which is reasonable) doesn't change the moral valence of going around regulations per se. What it changes is the reason why someone is doing it. The hypothetical NYC real estate developer is in no danger of starving, and indeed is probably pretty wealthy. So when he lies to get his construction project going, he's just doing it to line his pockets. But the hypothetical Soviet citizen is probably going to literally go hungry unless he does something to work around the system. So it becomes acceptable to do a nominally bad thing because the reason why is sufficient. Kind of like how stealing to plunder riches is condemned, but stealing to feed your starving family (or self) is generally accepted as ok.
Okay, so you are applying this logic to, say, tax loopholes and environmental regulations, and not, say, production targets or reporting to Comrade General. That makes more sense.
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