Brendan Nyhan compares:
[Reagan] is remembered as the so-called "Great Communicator," but that's after the economy picked up late in his first term and he won a landslide victory over Walter Mondale. However, Reagan was not always viewed that way -- he suffered through a recession early in his term that damaged his political standing (his approval trajectory was very similar to Obama's). The political scientist Jonathan Bernstein reviewed press accounts of Reagan from January 1982, and concluded that "Reagan's manner [was portrayed as moving] from amiable and clear on the big picture to clueless and oblivious to the important details of governing -- and indifferent to suffering -- when things were going bad."
The larger point is, as Bernstein notes, that "character traits are perceived by the press in light of how the president is doing in the polls and in Washington, not the other way around." In other words, the perception that Obama isn't "connecting" is a symptom of his declining political status, not the cause.
Lou Cannon makes a similar point at the Daily Beast:
A year into his presidency, not quite halfway through what would prove a 17-month recession, Reagan was in worse standing with the public than President Barack Obama is today. In the Gallup polling of 1982, his approval rating hovered in the low forties throughout the year, bottoming at the beginning of 1983 at 35 percent. This turned out to be the lowest rating of Reagan's two-term presidency but at the time many who worked in the White House were privately betting that he wouldn't even be a candidate in 1984, let alone have a second term in the White House. His aides' gloominess was reflected in my reporting for The Washington Post, for which I was senior White House correspondent, and also in a book that year in which I predicted that Reagan would not run.
And somehow I suspect that at that nadir for Reagan, commentators like Krauthammer and Gerson and Brooks would not be advising him to heed public opinion, give up on his agenda, and recognize that it's madness to push through policies that were broadly unpopular. Au contraire. Fight, Mr President. Fight. In the end, even the conservatives - perhaps especially the conservatives - will respect you for it.