If he's hoping to use baseball as leverage to get into a highly selective D3 (NESCAC schools, for example) then yes, HF in November would be a problem, as the coaches at those schools will want him to apply ED. If the schools are not as hard to get into, or his academic credentials are such that he's a good bet to get in on his own applying RD, then November would be fine.
If the money is there, maybe do summer and November.