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Jack said that there two sides to the ledger with respect to tobacco

And I replied there were similarly two sides to the ledger with respect to many other drugs.

He didn't say which side would necessarily prevail in this case.

Neither did I.

Furthermore, there is no reason why the side that's stronger for one drug is necessarily stronger for another.

Are you saying that out of all existing non-legal drugs, not even one would have a similar profile to tobacco?

This would likely be true of many other (hard) drugs if there had been a history of legally selling them instead of nipping their markets in the bud. In fact, this would probably be true of wireheading too if it was practical, and ultimately, orgasmium. Willing to bite that bullet?

Go one step farther. Do that compulsion to agree and be mellow with people you don't agree with mean you're a dishonest jerk who's trying to manipulate them, or does it mean you're not feeling comfortable with disagreeing with them (for instance because you feel like they'd reject you if you did, which might be painful, or because you do not want to hurt their feelings, or because you feel like you don't have the social status to do that). Don't necessarily assume you're evil.

For instance I know I hate lying mostly because I am feeling insecure enough to think I wouldn't get away with it. This stems from a difficulty to put myself in other's shoes. If I know how and what I lied about, then surely I can imagine many ways in which they'll eventually uncover my lie.

Another reason why I may come to dislike social relationships is because I harbor few illusions about human motivation and drives. Most interactions with people can be interpreted as manipulation to get your way, if you try hard enough to see it that way. My issue with that is, however, that I don't want to have such a relationship with others. I naively crave a natural, hassle-free relationship where I'm being liked and like others unconditionally. So whenever I think in terms of what strings I need to pull to move others, I feel bad about it because I don't want to have a relationship with puppets, I want to have a relationship with real people. Yet, I can't exactly believe relationships are magical in that way - nothing is for free or unconditional, and there are definite winning and losing moves in social relationships. So I'm torn between what I want (not over analyzing stuff and just getting along with people) and what I believe (that if I don't do that, then I may fail at being adequately social).

Quite a few associations rooted in transhumanism have attempted (whether they did so successfully is questionable) to distance themselves from the crazy-sounding (to a mainstream audience) plain description of their original goals and beliefs, in an effort to attract more and better quality funding and following (such as academia).

Compare :

Longecity, formerly The Immortality Institute

Humanity+, formerly The World Transhumanist Association

The Singularity Institute remains named so, but seems willing to follow suit.

I think I'm observing an emerging pattern, where several loaded topics such as transhumanism and cryonics have become much more controversial and unfashionable in places which previously championed them, and Lesswrong is no exception, as there's been concern that such topics may not have their place on a forum devoted to rationality.

You appear to express this connection (transhumanism being unfashionable) yourself in this sentence : Denotationally crazy political (namely, transhumanist) rhetoric.

Is it me or has transhumanism become a taboo word associated to low status crackpots around here?

and I have seen Fermi estimates for quantities like e.g. the mass of the Earth apparently extract narrow and correct estimations out of the sums of multiple widely erroneous steps.

out of how many wrong/wide estimates using the same method?