There's one thing that doesn't add up: why would such a privacy conscious man use his real name on a project he thought might be illegal? If he was so serious about his privacy, he would not have used his real name in public.
Usually the simplest explanations are the right ones. Who expects to create a new form of exchange, that goes on to become a $10 billion network (and maybe one day far larger)?
It's entirely plausible that Satoshi thought using that name, on his little project, would be enough. There is sometimes a lab mentality among people whose work has mostly been hidden away, they would never expect it to touch every corner of the world economy. It was just an experiment early on, and by the time it was obvious it would be more than that, his name was already attached.
That's easy - bitcoin isn't and never was about "privacy". It was about defeating that supposedly-horrible "fiat money" and the associated inflation. It's always been more about escaping government-backed money. From the very beginning, when selling the idea of bitcoin, the true believers praised the lack of regulation and how your money wouldn't lose its value over time. Privacy was secondary, if mentioned at all.
I suspect the Silk Road connection is what popularized the idea of a public ledger somehow providing privacy.
Being a private person doesn't necessarily mean that you go to great lengths to conceal yourself. It just means you don't offer more for free, like posting your personal life all over Facebook for example.
