Doing all the necessary 'homework' still guarantees nothing. The initial post by Fungo talks about the variables. There are so many more variables than are ever discussed here. These kids are living (usually away from home) in an entirely new environment and associate with so many people other than their coaches and teammates.....teammates they may have not expected to have to relate to.
Similarly, the coaches who recruit kids do as much homework about the players as they can. Even when both parties do their homework nothing is guaranteed. Many times during the recruiting process the player (and parents) put on their 'courting' faces.....then when they arrive on campus to live 24/7 they just don't seem like the same people.....just as some parents/student-athletes think that the coach is not what he seemed to be while recruiting.
This happens in life outside of baseball as well. A guy dates a woman for a couple months, on an almost daily basis (probably spending significantly more time than parents/players/coaches spend together during recruiting).........all of a sudden the woman shows that she isn't what she seemed to be earlier (ladies, I know it goes both ways), and the relationship is either nurtured, somewhat crippled, or ends.
A transfer isn't necessarily due to poor planning or education. Sometimes what initially seems like a good fit just doesn't really fit.
I didn't know if my son's choice was going to be a good fit or not, and he is a junior now. There was no 'we' involved. The coaches are not coaching me; the faculty members are not teaching me, and the roomates/classmates are not interacting seven days a week with me........it didn't really matter to me if any coaches told him that he would play a lot, or a little, or have to earn his time. I know that coaches make all their players earn their playing time (coaches want to win), and I knew that my son had the ability to pitch for any school in the country.....but that he would still have to earn his innings by performing on the field, in the classroom, and in social situations.
An 18 year old kid needs to be able to adapt to any unfamiliar situations and even an unexpected environment, to negative coaches and teammates and even undisciplined teammates and friends. Our kids truly make their own beds and then have to sleep in them, just as we do.
If things don't work out at one place, perhaps a change may be in order. It doesn't mean that homework wasn't done with enough detail, though that can happen.....it just means it wasn't a good fit at the time.
I have dated women for significant lengths of time, and did not stay with them. The time for homework, self-reflection, and needs analysis really may never end, in all areas of our lives and those of our kids.
When things do work out, whether there are struggles, changes in plans or not (ie. transfers), then we can be.......grateful