And not even then.
It's always bugged me how many shit writers and editors are in the industry who just cannot wrap their heads around a character having a good life outside of superheroics and think that misery = good character development. The reason Born Again is such a classic Daredevil story isn't because Matt loses everything, it's because after he does, he picks himself back up, gets back with Karen, and starts to get his life back together. But then Ed Brubaker took the wrong lessons for his run because every arc ends with Matt worse off than he was before until the only thing he has left is to go join The Hand.
Sure, put the hero through the ringer occasionally, heroes need to be challenged to be interesting, but you need to make sure they come out the other side having learned something, or gotten stronger, rather than it just be fucking with the character just for the sake of being edgy.