Campaigning and governing are too very different things. One is sexy and draws the attention of very talented people for a limited period of time. The other is boring, bureaucratic, (probably) extremely frustrating.

Not really. The campaign is centered on a single objective, that of victory. the government tool has to be forward-compatible for decades to come, not to mention that it is subject to Congressional supervision and so on. If it was run like an agile development project then there'd be loud screams about the lack of accountability, process, etc. This is a 'big iron' project if ever I saw one.

Not really, neither the environments nor the personnel directly involved on software development are even remotely similar between the campaign and the executive branch.

The health care site involves a web application with high number of business rules and data structures.

The campaign's site is fluff.

Only people who don't know how the government works.

Campaigns are private entities designed buy a couple people to win

Governments are huge entities, with laws that look like they're there to protect public trust, but are really written to often reward key players (for this area of government).

Well he promised to close Gitmo too...

If someone does a bad job on a campaign, he gets fired and replaced with someone that can do the job better. Campaigns run on a limited budget - they don't have all the money in the world. They have a well defined goal and strict timeline.

Pretty much the opposite of a government project.

There's a big difference in the amount of bureaucracy needed to organize thousands of volunteers doing one thing versus millions of employees doing an uncountable number of things.