My DD20 did 3. The first was in December, the first date after taking the PSAT and then I scheduled the very next 2 dates, which were March and May, I think. They May was tough because she was getting ready for AP tests. I had read something about scheduling 3 successive dates because the process and material would be familiar enough and with the 3rd test already scheduled there wouldn’t be any pressure on the second score. As far as prep, we used a private tutor who targeted exactly what she needed to work on. The strategy worked for us because she surpassed her target score and had a pretty big score increase by the time she was done. She is pleased as punch right now because her friends are all trying to squeeze one more date in and she can just focus on applications.