Hard to know without seeing the terms of the contract.
But here are some aspects which I think work in Rashada's favor.
1. With NIL becoming more accepted and acceptable, it is not crazy for a judge to rule that the NIL offer had a material and direct impact on the choice of one college over others (and NIL offers from others), even if the deal is not "pay-for-play".
2. The timing of the flip was very late in the day. In other words, if you make an offer in November that requires a signed LOI in December and enrollment in January, it is not the type of timing that allows a polite "hey, we reconsidered the terms, let's both walk away" while giving Rashada a lot of time to find another comparable offer. In this situation, Rashada has already spurned the Miami agreement for the "better" Florida offer, and given the NCAA calendar of visits, commits, signings, LOIs, and enrollment, the late timing really is not something that would lead a judge to sympathize with Florida.
3. Rashada did everything he could do to meet his end of the bargain. He signed an LOI with Florida. He was in Hogtown in January to enroll. It is amusing to see that the less-mature, less-sophisticated party in a contract is actually the one who behaves and comports himself better in the process.
4. If the court WERE TO rule in Florida's favor, you would have to ask yourself "why"? Now that the NIL agreements are becoming commonplace, to rule AGAINST Rashada would be tantamount to saying that NIL agreements aren't worth the paper they are written on, and it creates an unnecessary and chaotic "buyer's remorse" situation that would be inherently unfair to the individual players who agree to such deals.
I would imagine that Florida and Hathnocock will settle.