At this point in time, I would not think about the draft, this year or next unless he gets something as well school paid for. If you think that D1 has a lot of guys, professional ball is worse.
As a player coming from JUCO, I believe after the transfer to any 4 year he can ask for a reclassification. That would make him a sophmore. Is the D2 willing to cover everything for at least 2 years? As far as the D1, if he has signed an NLI for 2 years and can get hitters out, go.