I don't mean to beat a dead horse but Ill chime in as this particular question and/or dilema is right up my alley. lol.
It seems when I left home as a young 18yr old to Marine Corps bootcamp that I never remember having any troubles that some youth do today, i.e. missing home, adjusting, social skills, meeting/making new friends, etc. The Drill Instructors made sure that I had a busy day beginning at 4:30am each day so I couldn't dwell on these things!
My son struggled in various ways as a JUCO freshman last year in ways that perplexed me and his mom. A kid can appear normal and seem to have everything going for him in the confines of his home, school, and surroundings. It's only when he/she leaves that they/us begin to learn their strengths and/or weaknesses. After struggling academically both semesters due to the new rigors of college baseball, this semester he boasts a 3.95gpa. What a year of maturity and experience make.
Bottom line. My son needed the JUCO route to enable himself to grow academically and figure things out. Being a starting pitcher in high school he also learned how to become a role player last year coming out of the bullpen and/or closer role. He did ok. Not great, but ok. His opinion. This year as a sophomore he is slated to be one of the three starting pitchers on weekend conference games. He figured it out during the season and off season.
Like others have said on here, there are SO many reasons kids choose 4yr schools or JUCO. The program, the coaches, the opportunities, the playing time, draft, buddies, girls, location, school reputation, academics, dream, etc etc. What one cannot prepare themselves for is the unknown, i.e. missing home, g/f back home, don't like the coach and/or players for various reasons, hate the school, bad professors, roomate, cafe food, no cable, etc. and thus, they begin wanting to either come home or go somewhere else. It happens.
I know someone suggested to me a long time ago on here to sit down with my son and make a list of pros/cons on all of the above and put it in front of him and get his opinion on each one. It made him "think" what his decision was about, and to "think" about these things from outside the box.
Drillerman, your post asked about playing time behind another player. When he is on the field and looks to his right and his left, he is going to see kids as good or better than he. For the first time he will understand what the term "sink or swim" means. It will help begin to define him as a young man and setting goals. If he decides to leave after seeing he is #3 on the depth chart, does it mean he is a quitter or weak? No. He may see something that you can't from home. Encourage him and support him, and listen. I'm a firm believe that when one door shuts, another opens. But he has to twist the door knob!
As a parent, help him come out of the clouds for a moment and look at the very real possibilities that it could happen and to know how to deal with it when he sees the signs. He'll be thankful you did.
Ok. I'm hopping off my soap box now! lol
YGD