Eh, sometimes. Average people are retarded. They want big government programs but they don't want to be taxed in order to pay for it. Average American has how many thousands of dollars of credit card debt? Average person is also uneducated and about 40% of the US is working at jobs paying $12/h or less. I can understand why government people wouldn't be completely transparent about everything.
That's not just Obama, that's for every politician.
Every President faces an issue of 'what not to tell the American public'.
Perhaps the most famous is FDR's running on a platform not to get involved in WWII, which the public did not want to get involved in, while preparing to do so - and using Pearl Harbor to get the US committed to the European war against Germany (shades of 9/11 used for the war in Iraq).
Of course, this is almost never a popular behavior to defend - citizens are not too crazy about saying 'ya, hide info from me' - but it is an issue.
For another example, during the cold war, Presidents and USSR leaders sometimes understood each others' internal pressures better than they got along with their own governments. They could discuss things in private communications at times in terms of 'I know you have to do X and Y or your generals will go after you'. Hence, for example, why JFK ordered his government not to gloat publicly over the USSR's withdrawal of missiles from Cuba.
Sometimes, it's easier to defend; not many today would not sympathize with FDR recognizing the need for the US to get involved in WWII against Hitler. Other times - probably most - it's not as easy to defend, e.g., Reagan's Iran-Contra policies that violated the law to sponsor terrorism against Nicaragua (and bringing cocaine into the US, leading to much of the new crack epidemic), or Ford's secretly approving Indonesia misusing the weapons we gave them for a slaughter in East Timor of 250,000.
It's just too tempting for politicians to misuse attacks around issues like this.
In congressional elections, Republicans attacked Democrats with claims that the Affordable Healthcare Act would reduce Medicare benefits - because it was politically advantageous for them to do so, acting as the protectors of the popular Medicare program. Nevermind their plan to slash it soon after.
On the other hand, I don't think Obama was exactly forthright about his plans for trying to get healthcare by selling out the plan as much as he did.