Stupid Oreki, not having the guts to go for it.

Still, this leaves a 2nd season possible (and likely, because this is KyoAni and will probably rake in cash) so I am all for it.

I can't help but think that Oreki would do much more good in law enforcement or something that makes use of his deductive skills. Business accounting isn't really going to maximize that, but having Eru as his wife will make sure that hole is covered.