Obama had envisioned that the arrival of the Affordable Care Act's major benefits in 2014 would be like a national seminar, showcasing his philosophy that government can and should smooth the rough edges of an unforgiving economy for struggling working people.
The goal was that in a midterm election year, Democrats would be able to point to millions of newly insured Americans, thanks to subsidized private plans and an expanded version of Medicaid. Media reports would feature compelling cases of people literally handed a lifeline.
That's indeed happening, but it seems to be only part of the story. The Republican portrayal of the ACA as government inept and out of control appears to be unfolding right alongside.
Although the stated goal of the law was to cover the uninsured, at least 4.7 million insured people had current individual policies canceled that didn't measure up to new requirements. That forced an apology from the president, who had famously promised that "If you like your health plan, you can keep it." It remains to be seen how many of those people suffer a break in coverage.
Americans with job-based health plans are also worried. A recent Associated Press-GfK poll found that most people who've seen their employers scale back coverage blame that on Obama's law, even though the trend of businesses shifting health costs to workers predates the law's passage.
It may take years to settle the nation's divisive debate over health care.
For now, administration officials say they are just focused on getting through the March 31 end of open enrollment season. People who enroll by that date will not face the law's tax penalty for remaining uninsured.
The two main objectives are to minimize any coverage disruptions around the new year, and launch a big push to get younger, healthy uninsured people to sign up. That's key to the law's long-term success.
Experts say it's likely that a big proportion of those who have signed up so far are people like Kraft, the disabled former bellman.
He had an urgent need for coverage because of his painful condition, and because the temporary coverage he had been buying through his old employer was expiring at the end of 2013.
Kraft estimates he spent at least 20 hours over the course of two months dealing with website woes that left him frustrated. But, in the end, he prevailed.
He says he's got better coverage than he had through his employer, and, thanks to tax credits, it's costing him about half what he was paying before. The only drawback is an annual deductible of $1,250, which has to come from his pocket.
"Once people are able to get signed up and they actually see the policies that are available to them, I think it is going to start changing minds," he said.