In my opinion you need to go into the conversation knowing exactly what your family can afford. If a couple thousand dollars will make the difference you stand a much better chance than if you are looking for 5,000 or more. When you talk about a $23,000 "gap" you need to know for yourself if that "gap" is the difference between your estimated family contribution or if that gap is above and beyond that. You also stand a better change of getting an enhanced finaid package if that "gap" is above and beyond what your family is expected to pay and not because your family cannot afford what is expected. You'll also be in a better position if you can honestly say to the college if they make a better financial aid package you will attend. You need to also be able to hold up your end of the deal if they make the offer.