In the early 1990s reformers also believed that the conditions were ripe for change; then, as now, soaring health care costs and growth of the uninsured population fueled public dissatisfaction

When Hillary Clinton was appointed chairwoman of the President's Task Force on National Health Care Reform. a Democratic Party staff member was quoted as saying -
"The health care lobby is one of the most formidable in Washington."
The 'usual' argument was made that -
"When liberals mean reform, they mean diminished excellence" and syndicated columnist and lecturer Cal Thomas stated "No matter what she does, she won't get the poor to stop smoking, lose weight, exercise more, give up fatty foods, or keep hypochondriacs from showing up at the hospital to be treated for hang-nails."

Since that time 'inaction and incrementalism have governed U.S. health policy, with the predictable result that both health care spending and the number of uninsured Americans have reached record levels' - New England journal of Medicine

I feel sure that Obama will also share the reality of Hillary Clinton's experience how great a challenge reform will be.
Two weeks after accepting this "mission impossible," she told a conference in Pennsylvania,
"It is a very difficult change to bring about.
The people who believe in changing the whole system ought to understand how difficult it is going to be to change even small parts, because of the interests that are arrayed against those changes."

The Clinton administration both underestimated the opposition and overestimated the support for reform

Jonathan Oberlander, Ph.D. writing on Learning from Failure in Health Care Reform in 2007 observed

"Firstly, in U.S. health policy, the status quo is deeply entrenched and, despite all its failings, the system is remarkably resistant to change, in part because many constituencies profit from it. Thus, although everyone decries the amount of money spent on health care, the political reality is that national health care expenditures represent income to health industry stakeholders, whose interests lie in ensuring even greater spending.

Second, many Americans are satisfied with their own health care arrangements, so reforms that threaten to unsettle those arrangements risk running afoul of the voting public.
Health care reformers must thread the needle by persuading the anxious insured that reform is in their best interest and that the uninsured can be covered without disturbing (and ideally, while enhancing) their coverage.

Third, expanding government authority over a health care system that accounts for more than $2 trillion and one sixth of the economy in a country that is ambivalent about public power is an inherently controversial exercise. No universal coverage plan, no matter how clever, can evade that ideological debate.

Fourth, paying for health care reform remains a formidable challenge. The Clinton plan collapsed largely because the administration could not secure congressional support for an employer mandate, but no obvious financing alternatives have emerged in the ensuing years, and persistent antitax politics and federal deficits constrain the options for reform.

Finally, the window for enacting a comprehensive plan for health care reform never stays open for long, so failure comes at a high price — namely, the loss of political will to do anything meaningful about the uninsured for some time to come.

The Clinton administration made no shortage of political miscalculations and strategic errors that helped to derail its campaign for health security. Yet it is easy to forget that Bill Clinton was not the first president to fail at health care reform: he was following in the footsteps of Franklin Roosevelt, Harry Truman, and Richard Nixon.

Ultimately, the demise of the Clinton plan says less about the administration's mistakes than it does about the extraordinary difficulty of adopting comprehensive health care reform in the United States.

For today's reformers, that is the most sobering lesson of all."