There is a tale in Greek myths of a woman who tricked Apollo into granting her a wish, grabbed a pile of sand and asked to live as many ages as there were individual pieces in the pile - yet she forgot to ask for eternal youth, so a thousand years later she was a dribbling and unhappy old hag desperately wishing she had died ages ago. I suppose something like this is what pictured by non-transhumanists when they speak of "too old" - and there is no obligation that your methods to preserve life will also preserve good bodily condition (not to mention Alzheimer-like thingies - what if the body does live but the mind deteriorates?).
It seems to be hard in practice to draw the line between "only picking certain bets" and "doing things I'm best at" (though the theoretical difference is obvious - maximizing P(win) by events and maximizing usefulness of one's skills to win by skills). The latter seems to be a good practice - yet your attack on the former seems to indirectly hamper it.
But modern society is an individual example of the general idea of society, whereas human psychology as optimized is a general idea (performed in every specific individuum to a certain degree).
Isn't the fact that we perceive all the quantities on a logarithmic scale far wider than the specific effects? We find it again and again and again, from sound perception to explicit amount perception to this. (Note that it is an even wider claim than mattnewport's.) So the distance between 8 and 9 years is not the same as distance between 1 month and 1 year + 1 month because the logarithms' difference... erm... differs; and suggestion to give something "now" is then just as infinite as probability 1.
"But I also benefit from the asteroid that killed the dinosaurs, in that I live on land that was formerly dinosaur-occupied" - you... do know that asteroid as a cause is unlikely, and something like volcano activity is much closer (not that it makes much difference to the argument)?
"And that is: humans don’t owe society anything. We were here first" - not true. Society as an idea was clearly established before human race, before language, before thought, it is an all-ape thing, maybe even wider. And (almost) every individual society is older than its individual members. And you apply an illegitimate operation of comparing the individual society with human as an idea. Maybe your idea in general is good, but you're using a wrong argument - incorrigibly wrong, as far as I can tell.
"And they should be allowed to form completely voluntary communities of icky people that enforce icky cultural norms and an insular society promoting ickiness, just like everyone else" - the child problem again. If a non-icky child is born to such a community, there may be little possibility to avoid it. Say, conservative parents are only going to subsidise their child's law school if it is the one they condone - the one with those rules - and the child is gay (or generally disagreeing with their agenda, but I believe the gay situation is more obvious because that seems to be inborn).
Despite science-fiction, I see little plausibility in hive rationality. So - and I may be putting my neck under an axe by this - I claim that no hive race could raise to getting anything near "contemporary technology". Also, most of the contemporary technology usable for colonizing is already costly and/or faulty enough that someone who is "paranoid enough" (and some Prof. Moody tells us there is no such thing - but still) would be unlikely to ever leave theit own planet.
"As well try to predict the warlike or peaceful nature of the United Kingdom by looking at a topographical map of Great Britain" - such things are _done_ and _super-done_. Mountains (and difficult-to-cultivate steppes? Is this maybe something about pastoring vs. agriculture essentially?) predict average warlikeness fairly well. Who were the most peaceful Ancient Greeks? Thessalians. Why? Thessalia is, like, the only place in Greece vaguely resembling a grassland, where all other Greece is covered in hills. Caucasus is one major battleplace for centuries. Sco'land? You bet. The East seems to be generally more relaxed, but still less so in Tibet than in Eastern China. Early-Rome-time Italy? Relatively peaceful Greek colonies in the Southern coasts, war-like Etrusci and Gauls and, certainly not the least, Romans near Appenines and Alps. (Note that Rome is relatively far from the sea, compared to usual Greek colonies.)
"It also brings together a group of people with some pre-existing common characteristics: male, nerdy, often abrasive, not very successful, interested in speculation, high-systematizing" - can male be an artifact of nerdy, abrasive, and high-systematizing correlation with gender? After all, as you note, when a girl accepts all the other things she is usually easily accepted, and gender is only a proxy for predicting the qualities.
"I think America has better values than Pakistan does, but that doesn’t mean I want us invading them, let alone razing their culture to the ground and replacing it with our own" - why not? No, seriously. America invaded several Muslim (fundamentalist Muslim, not we-kinda-like-Quran-stop-accusing-us-of-ISIS Muslim) countries already anyway. Why not raze the fundamentalist culture to the ground and replace it with universal?
"except that “race” is a much more complicated concept than ethnicity" - W. H. A. T. Arm people with five-to-eight differential features, and you get a good proxy for all the six main races AND predictions for unclear cases. I'd like to see you try doing that to an ethnicity (without language cheat, which is known to backfire).
"If you genuinely believe that facts and logic don’t work on people, you shouldn’t be writing articles with potential solutions" - I have seen people claiming things like "science/logic is only natural for people with schizoid tendencies and utterly unnatural for others". Given that "people with schizoid tendencies" (or whatever the right denominator) may be as much of a tribe dark-matter-like split from the rest of the world as your Red/Blue/Grey tribes you may get an illusion that people are generally convincible, whereas in reality it may well be just a feature of your own tribe.
And then the articles about people unconvincible by logic are written for the tribe's members as a guide to deal with the outsiders.