Note, though, that my playthrough doesn't involve Alison romance and Ian is still near-broke (he didn't do any spending on the bouncer or bad Jess etc) It is basically very easy for Ian to be completely out of money with just generic approach, and on certain routes he won't even be able to afford some stuff.
He doesn't have that many spending opportunities, this is true, but he also doesn't have many earning opportunities. If EK only gives him ways to spend money he has no way to earn, then it'll go tits up for him pretty quick.