Does a coach ever tell you what numbers they are looking for? My D was told that with a 31 ACT score it was recommended that she take the SAT as good scores on 2 out of 3 there are better than 2 out of 4 on the ACT. Also after she sent scores to several NESCAC schools, many told her to take it again despite her score as they look at individual sections in addition to composite. She would feel better if she knew what she was shooting for.
For what it is worth, the coaches in my kid’s sport have been quite explicit about the composite scores needed for admission and for merit aid, when merit aid is on the table.
In one conversation, after hearing the composite score needed, we asked if 1 point lower on the ACT would make a difference and the coach reiterated the specific score he identified as needed for admission. Our sense is, the coaches know what they need for their prospects to make it through admissions, and the NESCAC coaches were quite precise about the pre-read process and what to expect starting July 1. So, I suppose if, the coaches are saying to re-test, they are trying to help you put together the strongest admissions file so that there is less uncertainty all around.
Good luck in this process!