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So I just got accepted off the waitlist for a T-20 with 25K/year, but I am currently deposited with a peer school that is also giving me 25K/year after two rounds of negotiations (started at 20K/year). Can I still negotiate with the school I am deposited at for an increase or does it get annoying for the school to have to renegotiate this late in the cycle after already having negotiated previously? Both schools have around the same tuition, but the waitlist school has a lower COL. Any help would be great, thanks!

Annoying or not, you are already in. If you are respectful, you have only to gain.

Just be extremely polite and figure out exactly what the difference in COA between the two schools would be. If it's more than $20k, you can easily argue that school A (deposited school) needs to increase their scholarship to be comparable giving all the usual reasons: law school debt is life-changing, these are peer schools, etc. Just make sure you start off any negotiating letter with how much you love the school. And think about calling instead if you have to get an answer fast to your waitlist school.

Thanks for the responses guys! Just an update, I emailed the school I was deposited at and they upped the offer by a little bit. This was after 2 previous rounds of negotiation. Def. worth a try for anyone else wondering about the same thing.