Comment by gfodor

There are path dependencies. If the short term hack accelerates your ability to get enough traction to increase runway, you may survive to see the “right” solution implemented. whereas if you pursued the “right” solution more directly from the beginning, the additional delays would have killed you. Good technical leadership embraces the short hack and guides the project through righting it when the opportunity is there. (To fail to do either is an equal failure, and both are hard.)

Anyone claiming there is a clear answer to these questions is deluding themselves. Tactically, the best weapon is to recognize your own weaknesses, and it seems to me that engineers often have more of a bias towards performing tool and technology analysis and research in the name of avoiding the hard and often humiliating task of shipping software that users will almost certainly hate in its earliest versions.