WAIT here's my latest piece of olaf insanity. i feel like his fixation specifically on wealthy orphans is directly linked to the fact that he's an orphan, but not wealthy. he lost his parents, and gained nothing from it. in a way, he views the baudelaires and the quagmires as privileged or lucky, because they actually have an inheritance, whereas he lives in extreme poverty. he acts like a jealous child, explicitly remarking that the baudelaires are "selfish" for not "sharing" their fortune with him.
i think that is absolutely fitting of him. i think, of course, the connections with beatrice and others certainly drive his fixation on the baudelaires specifically. but he wants to benefit from them and get more than revenge!
there is a special sort of anger and jealousy here. beatrice made him an orphan, and he has been in the trenches since. now beatrice's children are orphans, and in olaf's eyes, they have everything. it isn't fair. they should suffer like he did.
very much the type of guy who thinks everyone should "pay their dues." there are a lot of older men in my field who make things harder for the student workers because "it was hard for us too," it's that type of energy. i hate it.
