Well, if academics are a priority over baseball that's another issue. JUCO to D1 or D2 is as common as a house fly. JUCO to D3 could be more problematic. Again ask the JUCO coaches, I will say that make sure you do not take too many classes in HS and make sure you get an associates degree from the JUCO. that will make transferring to a 4 year school easier. During the first semester of his second year in JUCO he will start getting offers from 4 year schools and you should ask the individual school about credits and transfers.