By Bertha Coombs

Even if HealthCare.gov worked as well as Amazon, buying insurance isn't easy. And for many young, first-time insurance buyers, trying to pick the most cost-effective plan can involve a steep learning curve. It's a key hurdle for Obamacare. To work, it's important that young, healthy people buy into the Affordable Care Act and get covered.

Thirty-year-old New York City real estate agent Michael Chadwick has been uninsured for more than two years, but he's been in no rush to wrestle with signing up for insurance. "I haven't really spent much time looking at the website and really focusing on the plans," he said. "I've just been focused on work." Chadwick has also been putting off medical care. He is overdue for a MRI screening, after having a benign tumor removed from his leg in college. (Read more: For young and uninsured, affordability is key) "The past couple of years I've been in that great bracket of making too much money to qualify for aid, but not making enough with all my other bills to afford health insurance," he said. 

Katy Irwin, a 28-year-old graphic artist, has put off getting dental surgery and buying insurance for the same reason. "I just haven't been able to save up the money," she said. Irwin told CNBC last month she doesn't think she'll be able to afford the new Obamacare plans, either, after looking at a calculator that showed her the cheapest options would cost her about $200 a month.

We asked Irwin and Chadwick to explore the plans on their state's exchange known as New York State of Health, which has not suffered from the technology issues that have plagued the federal marketplace HealthCare.gov. Irwin's search came up with more than 70 plans, with wide variations in monthly premiums, annual out-of-pocket costs and copays. She admitted she was a little overwhelmed by all the numbers, and was thrown off by the monthly tax subsidy calculation.

"I was excited at first because I mistook the tax subsidy that I'd get, which is $65, for how much I'd have to pay. And then I was gut-wrenchingly sad when I saw that the cheapest plan I could get was $307," she said. (Read more: Obamacare fix puts insurers in a tough spot) 

Her most affordable plan option with lower deductibles and dental coverage came with premiums of more than $300 a month, after her tax subsidy. But because she's under 30, Irwin also has the option to buy a low-premium, high-deductible catastrophic plan for less than $200 a month. She can add dental coverage for another $26 a month. "With catastrophic, I'm not spending a catastrophic amount of money," she said.

Chadwick's search produced more than five dozen plan options, with premiums ranging from about $200 a month to more than $500 a month, after the tax subsidy. He's leaning toward the cheapest plan, but it comes with higher out-of-pocket costs.

"I hardly ever get sick, I haven't needed to see a doctor in over two years" he said. "The biggest thing for me was MRI coverage." 

Experts Weigh In

We asked Mike Fortner, a broker at online insurance brokerage Gravie, to look over the young freelancers' plan options, both on the New York exchange and off of it, to see if he thought they had made the best choices. Fortner found that Irwin's catastrophic plan with a dental supplement would be a cost-effective option for her. She would have to pay as much as $6,300 in out-of-pocket costs if she had a major medical problem, but she gets a little more coverage than meets the eye, if she remains healthy. "When we dug deeper into this one, and as long as she stays in the network, the first three visits to the doctor every year are free," he said.

For Chadwick, who needs access to MRI screenings, Fortner said a midrange plan with lower copays could offer more benefits to him. "He can have a little bit higher payment each month to the insurance company, but when he goes to use the insurance, the payments will be a little bit more affordable," Fortner said. 

Like Throwing Darts

Columbia University professor Eric Johnson studies how consumers choose insurance coverage. He said even people experienced with buying health insurance are often making little more than an educated guess when it comes to choosing their most cost-effective options. "They're basically almost as accurate as if they were throwing darts," he said. (Read more: Insurer makes Obamacare the punchline in new ad)

In a report titled, "Can Consumers Make Affordable Care Affordable? The Value of Choice Architecture," Johnson and his colleagues found that consumers often put too much weight on out-of-pocket costs, paying for more insurance than they need. While comparison tools and calculators can help consumers make better choices, most of the new exchanges don't have those functions. "We've calculated that if you actually do websites right, and include the kinds of things that help people make better choices, every year it would save the government—that is us—$9.5 billion," Johnson said. 

Tax Subsidies vs. Tax Deductions

Under the Affordable Care Act, individuals whose adjusted gross income is less than $45,960 qualify for premium subsidies in the form of a tax credit that can help reduce their monthly payments. Both Chadwick and Irwin qualified for the subsidies. But as self-employed freelancers, they might be better off deducting the cost of their premiums when they file their taxes, which could lower their overall tax burden. They can't deduct their premiums, if they take the tax credit. 

"If you claim that advanced payment on the credit, you can't double dip," said Brian Haile, senior vice president for health-care policy at Jackson Hewitt. 

—By Bertha Coombs. Follow her on Twitter: @berthacoombs.