There should be no expectation that it will be easy.....none. These are only my observations and it hit me like a punch to the gut seeing it first hand. My point of view comes from observing a West Coast academic D1 program (non Power 5).
1. If he doesn't get cut in the Fall...great
2. If he maintains decent grades...great
3. If he makes the team and is not asked to redshirt...great (redshirting as a freshman however may actually be the absolute right thing for some). On my son's team, a few of the freshman who redshirted left the program the following year for JC ball.
4. If he makes the travel roster....great (not all players on the roster travel with their team. Several players are left behind at campus, which sucks but it's a numbers game).
5. If he is included on the active game roster...great (not all players on the roster are added to the active game roster - this includes home games).
6. If he gets some playing time...great. At higher levels, most freshman have a very tough time finding the field. The "Perfect Game #7 ranked SS in the state" getting playing time over a 22 year old redshirt junior is simply not the norm.
7. If he is handling the workload of being a student athlete and is supporting his teammates (especially his freshman teammates), while getting support back from them, then that's really great.
The way I put it is that it's a mountain to climb, but your son can do it. After he climbs the mountain, there will be another mountain to climb, only difference is that he will be much stronger and smarter, which will make that mountain and the subsequent ones much much easier. Good luck!!!!!
WCP