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If I do have to ask for permission from the universities, does anyone know if this is an easy process?
You should seek the permission of the university/college. Either go straight to the top and contact the Dean's office, or ask the Coach. Explain clearly why and in what context you want to use it. These are the two key factors in determining whether they should grant permission.
It should be a case of simply asking and, once you've clarified exactly what you intend to do with the logo's and the context they'll be presented in, being granted or denied permission. However, some educational establishments can have a tendancy to be overly bureaucratic.
If this is the case you'll find that their main concern is whether your site will be 'appropriate', ie, will the site and its content stay within the realms of accepted decency - theirs, not yours (foul language, innuendo, offensive/libelous comments, etc).
Relative to your questions:
a) No, you may not freely use images of uni/college badges/crests/coats of arms/insignia, etc. They are the property of the respective educational establishments and are subject to copyrights.
b) No, that is extremely unlikely. Anyway, why seek to pay for something you can get for free?
If you can make a good case for visibility on your site being good exposure for the school, you might also try approaching the PR department. In fact, at the university where I work, the guidelines for using university graphics are on the PR department's website.
And, yes, there are guidelines for using the graphics - a long page of them - even for people who work for the university. We do have a seal, a logo, and a graphic of the sports mascot, each of which has different guidelines, so we may have more than some schools.
Schools normally license the graphic(s) to companies that manufacture and sell t-shirts, buttons, bumper stickers, etc. Because of this, they can be "ouchy" about someone using them without permission and for free. IMVHO, your best bet is to show the school "what's in it for them." If they can see a PR advantage to being represented on your website, you'll be more likely to get permission. And if you can add a "used by permission" note to logos on your site, it can give you some cachet that sites using them without permission don't have.