| I don't know too much about Skidmore (and I went to Brandeis) but I'm fairly certain that Brandeis' academics are regarded as significantly stronger. Between NYU its a little harder to say. I'd argue Brandeis has a better academic reputation but NYU is still much better known, especially outside the East Cost.
As far as housing, reslife always says they've been in able to accommodate everyone on the waitlist. Even if you're on the list until August you'll probably get it eventually. Just be patient! Also, there's a new dorm opening for second semester so there should be definitely be room on campus then. Perhaps its possible to rent a room off campus just for 1st semester and then move on campus? It may be more complicated then its worth but its possible. Regardless of where you live, Brandeis is a very club-centric school. Everyone is really involved in one particular organization or club. If you get involved in one right away, its a great way to meet people, make friends, and become integrated in campus life whether you actually live on campus or not.
As for money, thats something none of us will be able to answer for you. I suppose it depends how unhappy you really are at Skidmore, if you think that there's anything you could do to improve the situation, and if the additional financial burden is worth finding an academic environment in which you thrive etc. | 
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