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.
(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.)
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.
...if they don't want to change. That is a true statement. But, if they do want to change, it's relatively straight-forward.
BTW the thing you can control is not your actions, or even your reactions, but rather your attention. The best thing a narcissist can do is learn to see themselves in others. Modulo the risk of projection (that is, ascribing too much commonality to the other), it's a nice judo move to turn a dark quality into a light one.
Yes, this is what stood out for me. OP sounds malcontented, and habitually dissatisfied with his role, and makes antisocial decisions (like spoofing numbers - which is not just dishonest but shows contempt for the target) that show poor judgement. He compounds the poor judgement by bragging about the previous poor judgement.
The antisocial stuff is implicit in what he doesn't mention: from his descriptions, his workplaces are hollow boxes with some juicy targets (execs) in them and nothing else. Where are the people? There aren't any because at some level they don't exist for the OP. This is, of course, a hallmark trait of narcissism.
The good news (great news, really), is that NPD is one of the most treatable of personality disorders if the person decides they want treatment. The reason? The narcissist is confident in their ability, and confidence helps when you want to shape your own behavior.
The caveat to all this being that free advice is worth what you paid for it, even less if given by a stranger on the internet. But, FWIW, it's my honest take. If it ends up being accurate (if you look up the disorder) and you get help, I'd love to know if this post help you. (See, I'm a little NPD too! ;)