Great discussion but it needs a little more depth from the big picture!
What is the time frame for success? Everyone using bitcoins tomorrow? Next year? by 2020? Without a goal, we have nothing!
Secondly, as many people have pointed out, Bitcoin is the Internet circa 1992 - I was there, it was awful. If we use this as a guide, then we have a number of hurdles to deal with.
Firstly, we are beyond the technical issues, bitcoin works as it should, and it can be tweaked for scale, just like the interest in 1992.
The current problem is legal, which the internet also had to deal with. Online copyright was a huge problem in 1992 - who owned what? What laws counted? Who was responsible if? etc - these are the same questions that bitcoin needs to address. Once that happens, then its the next stage, mass adoption.
In the UK, we had a number of ISPs who gave us the push to make the internet popular, the most famous being Freeserve. The downside of this popularity was that the freeservers knew nothing, and blocked up the bandwidth!
Who will be the market makers for bitcoin? We need to grow the current market from its 2 million users to at least a billion, if not more before bitcoin becomes something.
With mainstream we got economies of scale, and finally e-commerce stared making sense - and this only really stated happening in the last 10 years. Bitcoin needs to find its niche, which I agree is probably micro payments of less than $100 a deal. It needs to be better, and cheaper than paypal - and be able to prove it to anyone who doubts it.
There is a huge difference between being an asparagus type geek who can handle the foibles of bitcoin, and the rest of society. The mindset change needed to turn bitcoin into a a must have useful and appealing tool of the mass market is so big, I can't even start to describe it. We are talking about thinking like a 15 year old girl, and getting her to expect to use bitcoin everywhere - because she finds it better than anything she currently uses!
Please don't think I'm being ageist or sexist or whatever offensivist I might be! The point is that mainstream take up has far more 15 year old girls than it have technical libertarian geeky types.
Once we turn that corner, then the son of bitcoin will be in every digital wallet on the planet, but in reality, its not going to happen until at least 2025!