Obamacare is probably the best system for covering people with preexisting conditions and extending coverage to lower income folks who can't afford market rate premiums. Problem is, someone does have to pay for these things. The costs have to be shifted to folks who can afford more; upper middle class, wealthy and so forth. I think when these costs get passed along as premiums, the more fortunate folks get "sticker shock." It looks like Obamacare is terrible as their premiums go way up and their coverage gets less comprehensive.
Maybe it would have worked better if this cost shifting was honestly labeled as taxes, rather than trying to hide it among premiums. Economically, that would have made more sense, but politically it's, unfortunately, a nonstarter.
After Trump has rallied people against Obamacare, he and the Republicans are now stuck trying to fulfill their contradictory promises. Obamacare may have not been pretty, but it's a difficult problem that its been trying to solve.
In Canada, the healthcare is provided, for the most part, from taxes. Taxes can be graduated so more fortunate folks help out the less fortunate. Everyone saves some, in the long run as access to preventative care, across the entire population, improves. An ounce of prevention worth a pound of cure. Overall health improves and it's easier to keep costs down under the Canadian system. Short of something like that, Obamacare may be the best that this anti tax society can muster.