Sorry for the slight thread drift guys, but I have a question which I didn't think it warranted a new post.

I am in the position where I'm very unattached to my location and can choose to live anywhere I want for the long term. Currently in ORD but I don't want to buy property in Chicago.

Would it be dumb to choose to commute in exchange for a place I like?

In the interview they explained the X and Y list for open time pickups. Is it possible to still be able to make some extra money on the Y list in a heavily serviced destination?

Would you say that I am crazy for even considering the idea of choosing to commute?