Yes, there are cases where it’s wise to follow Chesterton’s advice. But many more cases where that’s just lazyness disguised as wisdom.
Chesterton's fence is about explicitly removing something. You can't implicitly invoke it.
What you're describing is a lack of explicitly removing things. Chesterton's fence does not apply here.
Still, I think we should sometimes be bold enough to call out when we think that the Emperor has no clothes. In this case, Chesterton's fence is much less deep than it's made out to be.
The guy who wants to take it down, that's at least a valuable proposition. He's trying to decrease entropy. He's at least trying to put up a fight with the natural state of affairs that things become more disordered, more cluttered, more messy.
The guy who shuts him down, he's lazy. He's not willing to put in the work himself to see why the fence is useful. He's putting the burden of proof on the guy who at least is trying to do the good thing.
And many times guy nb 1 will just say, "well then, I tried, but there's opposition, and I don't have the time and energy to fight this battle".
And the fence will stay there.
And for each 1 useful fence that should stay there, there are 100 rotten ones that shouldn't.
The thing is, this is so entrenched, that people don't even try anymore. Maybe it's Pavlovian.
I'm saying this: we should at least admire those who even contemplate taking down a fence. And those who take the risk to speak out that the fence should be taken down.
Instead, we admire Chesterton. Which happens to be quite convenient too. Because we are lazy.
Oh, don't worry, I'm lazy too. How many times in my life didn't I say "this is a need to have thing and this is a nice to have thing. Considering the urgency, I'll deliver the need to have one, and leave the nice to have for another day".
In other words, how many fences didn't I leave the fence in the road? I'm guilty. But at least, I don't feel proud and wise about it.
I also disagree with the specific claim that software bloat is due to repeated application of Chesterton’s fence; I think bloat is caused by a lack of thought about what is needed and laziness around pruning dead code, rather than thinking about justifications for past decisions and then deferring to them.
I’d be curious for contemporaneous accounts over someone a century later guessing what may or may not be obvious. Maybe a cabal of industrialists conspired. The Foreign Dredging Act does predate trustbusting. Or maybe there were military concerns. Not an issue in this particular case, but one can imagine outrage if e.g. China controlled the world’s dredging fleet and threatened to isolate America’s ports in retaliation for some Senator’s mean tweets about Xi.
From my readings, the reason certain parts of shipping are mandated to be constructed in USA is that we Americans don't want to lose the ability to construct war ships. Tariffs may not be maximally efficient from a theoretical free trade perspective, but the cost premium of a tariff forcing local production may well be worth it compared to losing your ability to protect yourself on the seas.
Now, whether you agree with that sentiment or not is orthogonal. Chesterton's Fence says that if you don't understand why this law exists, then you don't get to tear it down until you do understand why it was ever thought to be a good idea.