Often the good is the enemy of the perfect. Obamacare was such a joke that it set the Democrats back a generation. They managed to get something passed, but their clinging to norms and refusal to nuke the filibuster meant that the bill was a pro-corporate mess so convoluted that people didn't even realize they were benefitting from it. It legitimately helped people, but it also so sabotaged the Democratic brand that it set progress back decades in many fields. We got Obamacare, but we traded Roe v Wade for it. Without Obamacare, abortion would still be legal nationwide. People saw what Democrats would do even with a supermajority, and many voters just gave up on politics entirely due to Democratic corruption and timidity.