Lots of people here agree that something's very off with OP. Maybe it's not NPD, but there's definitely something. Could just be poor personal hygiene or social skills. Maybe he's asking for 7 figures at every first interview. Personally I'm very fascinated with the duality in OP's mind of either working at Google or being homeless, like the huge middle ground doesn't exist at all.

And OP seems very concerned about medical insurance, which might suggest something bigger behind the curtains. Young folks often think they're invincible, and medical insurance is last in their list of worries.

The OP asked for candid feedback, and told us not to hold back. I myself added a caveat to my post to address your very concern. Is there something more that you think I should have done?

(BTW I agree I'm reading a lot into his post, Sherlock Holmes style, but without confirmation one way or the other, its hard to say if I'm on target. In any event, I do not believe that the OP would share your umbrage, given his post.)

Yeah you should have given them advice on how to land a gig and not diagnosed them with NPD. I see where you're coming from and I agree it might be useful for OP to work on how they communicate, but that should be between them and a therapist.

There are a few assumptions that are false. For one, I am not a doctor, and this is not a diagnoses. It is explicitly an opinion based on (very) thin evidence. I agree they should see a therapist, if possible. I would not normally be so blunt, but the OP asked.

But the primary false thing I want to address is the tacit assertion that "Telling someone they have NPD traits is a personal attack." I understand that assumption because, sadly, accusation of personality disorder has become a common style of personal attack. It's very similar, actually, to the classic status of "homosexuality" - once a pejoritive, now mostly just a fact. And I'm not sure if you noticed, but HN has a LOT of psychology-related content. As a group people here seem to show a lot of admirable compassion and empathy for each other's vulnerabilities. I think it's a remarkable feature of the place, and I hope you can take my words in that context. NPD is quite common in the world, in our field, and its entirely posssible to be a good person who struggles with NPD.

Your protective instinct speaks well of you! But you may need to reassess whether or not I actually attacked the OP, given his request and the context of my response.