I think the fantasy about temporarily being the opposite sex is a lot like a man who wants to fly living in a world before airplanes and wishing aloud that his flying potion would work. What people want is possible in a lawful universe, but what they say they want is filtered through their intuition and experiences and as a result it doesn't make complete sense.

What people want from this fantasy is high-quality information on what a best-case scenario of medical transition would be like, and minimal side effects from acquiring that evidence. That seems like a reasonable thing to want. For any medication or surgery, of course you'd like to know before agreeing to it how it'd affect your life. And if you're trying to predict disasters in order to prevent them, letting a disaster happen and taking notes isn't a great information gathering method.

Baking a cake is the sort of thing I'd do for fun occasionally. If I were on good enough terms with someone that I didn't feel ick about being asked, I hadn't baked anything in the last couple months, and I already had all the ingredients in the house, I'd cheerfully bake someone a cake for zero dollars. Sometimes somebody gives you an excuse to do something you like to do anyway and that's mutually beneficial even without any money changing hands.

On your Pascal's Wager example, I don't think your "least convenient possible world" is really equivalent to the world I live in on every meaningful feature other than convenience. Selecting Catholicism out of all similarly complex stories would take a whole lot of evidence. So if Omega tells me the Catholic interpretation of Yahweh is the only plausible god and I completely trust Omega, I've been given a lot of evidence in favor of the Catholic interpretation of Yahweh.

Pascal's Wager is meant to be an argument for theism in the complete absence of evidence, not an argument for theism when you have almost all the evidence to prove that a particular god exists. We have perfectly good mainstream decision theory for what you do when you have evidence; nobody needs Pascal for that.

The way I solved the pen on the moon question is that I remembered the famous demonstration one of the Apollo astronauts did with a feather and hammer on the moon, and didn't think there should be a meaningful difference between those objects and a pen. I could've worked out the physics, but pattern-recognition was faster and easier. 

I'm fairly sure I've felt my ethical caution emotion activating when it really wasn't warranted by the situation. When I'm not dealing with an ethical question, I'm capable of overcoming it with significant effort. But when I am dealing with an ethical question I generally listen to that emotion rather than fighting it (hence why I wouldn't rob banks for the greater good even if I expected not to get caught).

I think a large part of the reason why a lottery with a 1 in 1 billion chance of destroying the world alarms me is that it implies someone built a world-destroying machine to connect to the lottery. Machines turn on accidentally fairly often. I've seen it happen more than once.

I'm not sure if this thought will come out right. But I recently had demonstrated to me that the Sequence on cults was actually onto something true beyond the scope of this community, not just an evil genius persuading me his cult isn't what it looks like. It's a relief, in a way.

I'd previously seen some unthinking allegations of cultishness in the LessWrong community, ones that looked exactly like the instinctive flinches from weird beliefs I'd read about. But I was on some level worried I'd been taught to unthinkingly dismiss valid criticism. I recently saw an allegation of cultishness around here that didn't seem unthinking, and it was uncomfortable to consider, and I'll have to look into whether I believe it or not, but I'm relieved I can tell the difference. 

Whether or not y'all're a cult, there's some good ideas here and I'm glad to have learned them.

If erasing the memories were done by artificially stimulating the mechanism that causes normal forgetting, I think they'd be the same person. After all, I don't consider myself a new person whenever I forget something. But maybe there's something I'm missing. 

I don't know if this will help, but I was noticeably better at thinking fairly about uncomfortable hypotheses for a while after some experimentation with psychedelics. That's actually when I realized I was trans. Maybe if the theists in question are the sort of people who use the right sort of drugs, you might want to try revisiting your discussion when they've been artificially made more able to consider frightening propositions.

On the other hand, those few months of being more open-minded were also a few months where I kept finding myself believing supernatural things that didn't make any sense. And I don't (as far as I know) have a very strong predisposition toward supernatural beliefs. So you probably shouldn't encourage your friends to drop more acid than they would without your interference; the nudge toward spiritual delusions might well do more harm than the openmindedness did good.

I think I agree with you about our invented reasons for instinctive emotional reactions being a big part of our experience of the emotion. I once had a panic attack from having to do some public speaking, but because I'm not consciously scared of public speaking, it felt to me like my adrenal glands had malfunctioned and pumped me full of adrenaline for no reason at all. 

I anticipate that if anyone ever gives me an unnecessary dose from an Epi-Pen it'll feel quite similar. It was uncomfortable, but I knew nothing I find horrible would happen to me, so it was much easier to bear gracefully than some other anxiety I've experienced.