Quin, it seems to me the essential problem is that Gerson and his ilk don't understand the "tough love" aspect of conservatism. They are so afraid of being perceived as hard-hearted and uncaring that they will compromise away anything in order to avoid that perception.
This is what I see as the contrast with Reagan, who understood hardship as an incentive, a motivator. The conservative believes that if you're poor, if you suffer from unfair disadvantages, if you have a few tough breaks, this should spur you to greater effort. In striving to overcome obstacles, we become better people, and the man who triumphs over adversity can take justifiable pride in saying, "I did it." If, on the other hand, government treats you like a charity case, so that you make your way in the world with the constant sympathy and assistance of the Nanny State bureaucracy, where is the self-improvement, where is the sense of triumph, where is the source of meaningful pride?
Reagan understood all this, in a way that Gerson obviously doesn't.