Fungo, great topic!
The "fit" is critical to all players/families. Be it playing time, academics, proximity, coaching staff, financial, getting to the next level etc. What is good for one student athlete is not necessarily good for another.
For my son, he chose the JUCO route over D-1, D-2 and D-3. It's a good fit for him, he likes the coaching staff, and he feels he can adjust to the college academics their vs. some of the schools that were interested in him for baseball.
"Fit" is critical and when evaluating all your options, don't just look at the baseball aspect. This a mistake that many players make and then they end up wanting to transfer.
JT made some good points about the recruiting aspect and "over-recruiting."