So at present it's Lily and run with the money?
As much as millions would be great to have the only thing I really need for my MC is the beach house.
With or without the money he gets to wake up with whatever woman he ends up with with the beach at his doorstep and an amazing view that would make the most sheltered of romantics cream their panties.
Even without the millions he has enough to live comfortably until he finds a job he enjoys and he has a home to live in.
The money isn't what will swing my pick of "main girl". There is just no denying that Lily is, effortlessly, the single most fun and sweetest out of all of them. Add in that she knows how to cook, takes care of herself and her surroundings and loves her friends .... she is WTHI's ultimate waifu.
Katie is very close but while her jealousy is contained it's still a emotion i'm not very fond of. While her plus points do cancel that out somewhat it is still a concern. That's more a me issue, i've dated a jealous girl and there are only so many "where were you, who were you with" conversations I can have before I start to go loopy.
Way I see it, i'm not a jealous girl, never have been. If someone i'm in a relationship with is going to cheat on me then me acting like a jealous lunatic isn't going to stop them. In fact that would more likely be the cause.