So the argument is that breaking a shopkeeper's window never makes sense even though it creates business opportunities for glaziers because the money the shopkeeper must spend on repairing their window could be spent on something else. Makes sense. But what if that something else is buying a prostitute, gambling or "investing" in stocks (i.e giving money to banks)? Maybe paying kids to break windows to create jobs for glaziers could be "good for the economy". At least sometimes.
On the whole it's negative. The more it's done the poorer we all become. And any indirect benefit (preventing infidelity or gambling through distraction/destruction) is so unreliable it's not a functional framework for progress.
The point of scientific inquiry is to make "claims" into "facts" by finding "evidence". We have a "claim", that breaking windows (always) "on the whole is negative". However, there is no "evidence" to be found. Thus, it is not a "fact". Modern societies are very complicated to just referring to "common sense" is not enough.
Increasing entropy in a closed system isn't progress except in the rarest of edge cases. You're welcome to burn your own house down and measure the consequences.