The heroes failed because none of them are experienced really. They think they have a good idea and ran with it against orders. It might have been a good plan, if they had the people to pull it off. but they didn't anymore. Finn knows nothing of the outside galaxy. Rose is there to give us a perspective of someone who actually has been in the galaxy her whole life rather than isolated from it like Finn and Rey. Poe is shown to be a hotheaded pilot like one would expect. The admiral doesn't tell him her plans because he will not understand them, and he doesn't when he finds out about them. If told about the sensor cloak, I imagine Poe would have suggested sending a team over to the Mega-class Star Destroyer to blow it up, even though the First Order can see the transports visually. Also I imagine they has thought there was a leak on the ship, a spy or audio tracker, since the First Order did something that was suppose to be impossible, track them through hyperspace (though Darth Vader did that with Leia between Rogue One and A New Hope). The difference was that they basically did it immediately, meaning there was nowhere for the Resistance to run and if they did, their allied at the other end would be killed by the First Order's fleet.