I know it's just a question but I don't really know how you got the impression he'd be "obsessing" over his looks from that post. Guys who think they're possibly attractive have to look in the mirror a lot, guys who actually are attractive have reality to remind them on a regular basis, and don't have to obsess over it.
Unless something like hair loss kicks in, then obsess over the hair loss but not exactly their facial features.
I think he was giving a nod to the fact that looks gave him a tailwind to improve himself in all ways, something a lot of less attractive guys on here rightly note as a reason for finding it very difficult to really dig deep in terms of self-improvement. They can pretty much only improve themselves in coping interests that make them genuinely happy, and a lot of the time these interests aren't exactly beneficial to themselves or to society, unfortunately.
If you have encouragement from doing nothing, you encourage yourself to do things you don't necessarily want to do or need to do.
It depends on the personality. I've known good looking dudes who constantly check where every hair is left hanging, complete nw1.
I'm pretty good looking myself, luckily, and I don't personally care about it much, all the time anyway. I'd say the only time I do is when I go out, looking for hoes, and am trying to look my best. But that's because I feel it's a done deal, no need to obsess, I'm good there.....except with this head of mine, that's in question, so I do think about that. A thick nw2 would make me stop thinking about it as much, as that would be the minimum to "be good" on that front.
And I've known good looking guys who just shaved their head and went with it, didn't think much about it (that I know of). When asked, just made a joke about how his whole family shaves their head, and that was it. Getting girls just fine (of course quality might in most cases be better if he had hair).