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I've been accepted to two academically comparable schools and have been offered a scholarship by one of them. I'd prefer to attend the school that hasn't given me any money for a multitude of reasons. I'm aware that people in my position have used scholarships awarded by similar schools to leverage their preferred destination into making offers, but I'm not sure when or how that process typically begins. I assume if I don't get any money from my preferred school there won't be a "you're getting $0 from us" email I could respond to, so presumably I'd have to reach out to the school, but I don't know where to direct my correspondence or when to reach out. I'm wary of reaching out too soon (i.e., coming across as coercive by asking for money before the school has even decided how much [if any] they're willing to give me) but I also don't want to wait too long and then find out the school's already given all the scholarships they can. Does anyone have any advice on how and when to get the ball rolling on the scholarship negotiation process?

Find out who your schools admissions director, financial aid director, or comparable postilion (fin aid coordinator, etc.) -- if nothing else see who the person is that has emailed you admissions correspondence. Contact them, ask them about timelines for things like scholarship and financial aid consideration, because you are trying to make an informed decision and you already have information from other schools and you have upcoming deadlines you want to be mindful of.

Law school is, among other things, supposed to be designed to teach you complex reasoning and preparation skills. Here is a small chance to show you already have some of those abilities. No one is going to fault you for just calling and asking, given you are a candidate they value (they gave you an acceptance) and they are invested in you matriculating. Also, these people are part of the recruiting/"customer facing" aspect of the law school -- it is good to be nice to them ... but by now means are they going to ever get around to telling anyone else significant in the law school that oh yeah "so and so was a pain in the neck during the admissions ans scholarship period" -- its two separate beasts. handle this, get as much as you can from schools while maintaining tact, and then move on -- once its over, its over and the real, actual stress of school begins. lol