Conservative certainty that Healthcare.gov's technical failures doom Obamacare has two big problems. One is that several state exchange sites work fine and are very popular, indicating that the federally run exchanges can work. The other is the stocks versus flows issue. With each passing week, Healthcare.gov does seem to be improving and the number of people who can use it is rising. The ramp is frustratingly slow, but the steady increase in the flow of people who are able to enroll means a constantly accelerating stock of enrollees.
So for people who want people to get subsidized health insurance, that's the good news.
But a cautionary note against people who feel a surge of optimism based on anecdata about the greatly improved user experience on the site: This visible consumer-facing side of the site isn't the whole picture. To truly work, Healthcare.gov needs to accurately convey subsidy information to people and then accurately convey enrollment information to insurers. These are, as I understand it, the more technically challenging aspects of the project. It's not "building a website" but "building a complicated computer system for which the website serves as a front-end access point."
The administration's official messaging about the status of the 834 data files that insurers need, in particular, remains pretty cagey if you ask me. But for people to get insurance, this has to work. And you can't figure out whether or not this is working by logging in yourself and doing a practice run-through. You would actually need to enroll and then follow up with your insurance company to see if things are on track.