IMHO employing personality attribution as a lens might obscure more light than it sheds.

I tend to prefer the ones we can tie to the thing itself, i.e. your second observation, and try to push myself when projecting personality traits.

FWIW re: your first observation, the sucking up phrase has a link to an OpenAI post-mortem for the incident they are referring to - TL;Dr training response to user feedback