Richard Zen:
Simon T.:
And yes, the weirdo factor is a big one, being on both side of it, as political-correctness come into play to give us the worse of both world. Non-weirdos are boring anyway and social convention are hindrance we should all wrong on.
My belief is that it will be a small population that will meditate (as has been always the case). Most people can function fine without meditation even if there's much room for improvement and most people I talked to about meditation kept saying the same thing: "It's brainwashing". That's the #1 argument against meditation I got. "Muaahahhahahahahah! BRAINWASHING!" I actually think mindfulness in particular is anti-brainwashing. It doesn't matter. You attack their egos and you'll just get blowback, and they will probably try and test your anger control to prove you wrong.

Most Dharma is spread by internet and books. People will need to try this stuff out anonymously and see some basic benefits before they join a Sangha. Online Sanghas with Skype and other technology are more likely to be tried because you can aggregate more people from around the world.
The other stumbling block is Dukkha Nanas which will block most people who try meditation. Few will even bother trying to get to equanimity. Then when you add the "it's brainwashing, and it feels bad", you can see how the low turnout manifests.
As you mentioned before there are views. Everyone has views including Buddhists so if people are dogmatic about practice then you lose another bunch of people leaving a small number of pragmatic Buddhists that tolerate the dark night and practice like a hobby. Disagreement is everywhere.
Oh here's a few more stumbling blocks:
-Meditators don't agree on politics and economics so that would have to be ignored. The focus should be meditation.
-Lack of time due to work.
-People moving to get new education or jobs elsewhere.
-People from different religions dabbling in mindfulness but reject Buddhist doctrine.
-Guru mentality (or fake Gurus) and people leaning on that (Bill Hamilton and Daniel Ingram have wrote lots about this).
-People who aren't serious about meditation and just want to vent their concerns and get attention.
-People who enjoy their hobbies and will never take the time to meditate.
-The cost of meditation retreats.
-Different meditation methods working or not working with different people.
I would just focus on networking with people (like on this site or elsewhere) and leave it at that. You can create a Meetup.com group in your area (or join one if it exists) and see who applies. I'm sure it will be a mix of the above list.
The reality is it's better to meet with like minded people about practice who volunteer to meet than worry about how our culture is made up. Culture is actually the most difficult conditioning to change and the only changes I see that happen spontaneously are when people pursue their desires. If people desire a culture change then they will change, even if it comes from desperation.
Finally I would say that we don't often talk enough about the end of a path and the ability to go on your own no matter what people you are near. Work and family forces us to deal with different people and opinions. That last thing we need is making instructors or other advanced practitioners a crutch to lean on.
I see that the "community" part of my post got more attention but at first it wasn't really the point I wanted to make. My point is that content matter. I got on this path when I was at the lowest point of my life and there was indeed a lot to deal with as some much had been accumulated over the years. Finally something that made sense. That is complete by itself and deal with the fundamental attention problem I had all my life. Not only there are plenty of techniques but there is also ways of measuring progress.
I'm immensely grateful for the people that meticulously documented all the stages before me has being able to track my progress and adapt my practice to the stages made a huge difference. Still, I have to admit that the "be your own therapist" mantra (there is a dharma book called like this somewhere) has his limits. Until recently, I considered the path to be my all inclusive solution to all my mental health issues. In a way, it is but in a way, it isn't.
Consider how Kenneth Folks was on anti-depressant until the very end, has he tell in the Buddhist geeks postcast. On one hand we have the stages that color our experience in such a way that it out shadow the details of our life at the moment. On the other hand, the is still such a thing as mood, positive and negative thoughts, optimism, self-worth, confidence. There is still a narrative being told in my head and the traditional dharma approach did very little to give a positive twist to it. I got acceptance. Sure. Like a ton of it. but acceptance alone doesn't cut it. Affects are being seen as they arise and I have become the calmest motherfucker in a 10 km perimeter. To a large extend, emotion isn't something that is subjectively part of my life anymore, outside the peculiar twist of the stage of the moment. To what extend is it a good or a bad thing that I sanitized myself so much in this specific way? Those are the things we are not very good at discussing as we don't have a framework for doing so.
Consider the ongoing debate on affect. I was listening to Kenneth Folk NYC dharma talk when he suggested that some degree of affect is necessary to feel compassion. If we are to have that discussion, we first need a language framework to deal with such things and the one coming from psychology and the one coming from the dharma are very poor at that.
I think it's Nikolai in a podcast that brought the example of the homeless man that we encounter on the street. I just don't see why I should feel any kind of negative emotional response to the guys situation. Quite the opposite. My odds of acting as a compassionate human beings, as opposed to simply feeling like I'm one, are much higher if a form of positive emotion arise from that encounter. I gained a lot of equanimity (as a general term) in the face of such situation. As I will progress, there is more of my stuff that will bubble up that will challenge that, for sure. Still, that's the direction this is taking so far. Is being equanimous truly the good of the practice?
From the initial emotional response to the situation, to the behavioral response, to the feedback emotion from the response, there is a whole world there to be described.
On my first retreat, I was with a Christan friend that just wanted to see what this Buddhsim thing was about. He was working for a Christian mission in Myanmar and basically trying to do the work of God, in his own way. After we when to thanks the abbot before leaving the retreat, he told me how he was repulsed by the guy. And he was right. And this isn't the only Mahasi student that give me the feeling that I don't want turn turn like those guys.
Kenneth get to talk about how the previous generation western Buddhists (read IMS) had the morality question covered. I don't know if he was just trying to be nice because I have a strong feeling that this is absolute bullshit. We have to give this to the Christians. They have a way to talk about morality in a much more mobilizing way. The road to hell is paved with good intention, indeed, but at least it give a sense of direction.
One of the reason that Richard developed AF is that the sense of mission didn't sit well with him. I'm really puzzled by what to do with this sense of mission. I got the feeling that I need to piggyback on this sense of mission for a while but it need to have a positive spine to it. I start to think that to have some kind of grandiose plan would be a good remedy to the mundanities of the layman life. Trungpa Rinpoche put it differently by saying that if you are about to get Enlightened, prepare yourself to become ego-maniac. It feels like if I keep this ego mania on leash, I'm condemned at living this path we some sort of latent depression, a feeling that I'm not living to my full potential. If I leave it wild, I expose my loved ones to sufferings I'm not quite ready mentally to handle, not that I believe it is my duty to protect their feelings. It feels like any kind of compromise is doomed. Either I keep mindfulness as my practice in a social world, which inevitably lead me to a more passive social role, or I rewrite the software to be uncompromising and voice my flawed opinions with all my weight to it.
It's probably a confusing post but those are confusing times for me.