Thanks everyone.
Follow up question based on what has been shared here so far.
If you were a mid major D1 talent level player and were considering a D2 because (1) academically it was probably a better school for you in terms of size and acceptance rate, (2) it was closer to home, (3) you probably would play sooner there as opposed to probably sitting as a freshman at D1 and (4) it was a D2 with a current 10 year history of being a very strong baseball program (with some graduates going on to play professionally), would you only go there if they offered you a share of one of their 9 scholarships (meaning that would be a sign that you wouldn't be on JV or just a player who never suits up)?
To your first question, you need to look at a lot more than roster size. How many do they bring in for Fall? How heavily do they rely on JC and dropdowns? How many incoming freshmen do they pipeline to a local JC come fall? How many typically get redshirt/greyshirted, etc. More importantly, how, where and when does the particular player fit? How does the school fit outside of baseball? You say this is a D2 close to you. Based on your previous persistent questions, I can't imagine you don't know more about this school than to rely heavily on roster count. Now, you may be able to extract more relevant info from roster makeup as you and/or your son likely know some of the players from your region and their talent level as compared to how much they have played and contributed. And, maybe most important - what does the direct dialog between your son and the HC and RC tell you and him about where he fits?
To your second question, there is often overlap with mid-major D1's and "very strong" D2's. I would suggest you remove the label from consideration in this instance. There is something that strikes me as a bit odd with the logic in your question... you say the player would probably play sooner but then you equate getting baseball $ as a sign the player won't be on JV or never suit up. If it were a scenario where there were two schools recruiting him from far away that only saw him a few times, I could understand that. But with a local target, the player should know the school and coaches and the school coaches should know the player. There should be ample opportunity for meaningful dialog. Do you know the player will play sooner or not? What D1 school are you comparing to? If there isn't strong expectation that the player will not be on the JV squad, you are likely fishing in the wrong pond. Pretty much the same goes for "never suits up". Yes, you want baseball money commitment as affirmation of their commitment but that isn't always in the cards. There are plenty of good D2's that have less than the full 9 scholy's and so any athletic $ offered is negligable, particularly for position players. Even with nine, that is not much to spread around to 30+ players. Yet, coaches can express in other ways their sincerity of commitment and belief in a player. That is an important piece that you should be looking for. Son got no money from a D2 but got every opportunity to play and contribute. Yes, he had to earn it, just as those receiving baseball money did. He pretty much knew each step of the way where he stood and what effort and performance level it would take to continue earning those opportunities.
Blanket statements can make things easy to compartmentalize but as TPM stated, each situation really has to be evaluated individually.