Yes I understand, you have presented that fact you have disliked certain cities and it has negatively effected you. BUT as undergrads, we have not experienced a schedule that dental schools give us. IMO, when you are in class 7-9 hours a day( more or less), and you are studying 2-5(give or take) hours a day, you wont have the luxuries of actually enjoying/not enjoying your location as we do in undergrad ( from what i hear from dental students, they had for more free time in undergrad).
Situations: ( - indicates that its a negative impact, + indicates a positive impact).
A. Go to more expensive school, and you are happy -+
B. Go to more expensive school, you are unhappy. - -
Expected Value: -2
C. Go to less expensive school, you are still happy. + +
D. Go to less expensive school, you are not happy. + -
Expected Value: +2
These expected values are under the assumption that you value both these factors equally. If you do not, redo the math, plug and chug.
My point is: from what i hear from dental students, and from our own life experiences, the students/people you are surrounded with are far more significant towards your happiness than the actual location.