Other Web Problems not related to Healthcare.org
The faulty launch of healthcare.gov reminds me of some other web problems I'd like to complain about.

The Unparseable Resume
It has been about a year since I submitted a resume, but I'm going to guess this is still happening: Every job application asks for you to upload your resume then proceeds to insist that you fill out a detailed form on your work experience and skills... the precise batch of information which is on your resume.

Below is an image of what happens when you upload your resume to Careerbuilder.

This problem is vexing because the website user is out of the client seat. He is in the position of asking for a job, so he doesn't have any leverage to complain. If he was signing up for a Spotify account, he might just abandon the application at this point. If an applicant can't be bothered to fill out these redundant data fields, maybe it would be better to just hire someone else.

Income Tax Return
Hundreds of millions of American citizens are required by law to file income tax returns every April. They do so not through the IRS website, but using a $50 software program, Turbo Tax or Tax Act. Below is an image from the IRS website:

In this example, the tax software industry was already up and running before the federal tax website was in wide use. In 2013 there isn't much incentive for the federal government to re-invent tax return software, putting Tax Act and Turbo Tax out of business. In addition, tax software is usually designed to help the client get as much money back as possible, which seems like a conflict of interest for the federal government.

These two are examples which have made the greatest impression on me. I say let's fix Healthcare.org and these other two as soon as possible, and we can have a great big party when it is done.