azcoyote,
This is one of those scenarios that is going to vary dramatically due to many, many variables, goals and circumstances even within the same family. My wife and I decided to help our kids the best we can based upon their situation, and our financial situation. We gave them some skin in the game too. My oldest (senior RHP) will most likely graduate with between $13-15K in debt, and pay it off immediately. He accumulated enough cash in summer jobs and internships that he'll pay it all off right after graduation. He decided against playing summer college baseball. It was not an easy decision. He's an engineering major, and will start off with a job at graduation with no debt. For his situation, an Ivy engineering degree was well worth the investment. Everything was need based financial aid at his school.
His younger brother is at an ACC state school (not playing baseball) studying engineering also, and working on campus to help pay his way. He receives no FA. He has a savings account that will cover the expected $10-12K of debt he will accumulate by this senior year. He has a summer job lined up for the next couple summers. His junior year he'll need to find a junior engineering internship. We fully expect he will have a job at graduation will no debt either. We're working on a plan for my youngest son (non-engineer), but that is in the works at this very moment.
One of the challenges that my oldest son faced was whether or not to play to summer college baseball. His college coach made that entirely his choice as do most of the coaches in his conference. It was a question that I posted on HSBBWeb many years ago, and it truly was a difficult decision for him. On one hand you have rising college costs, on the other you have (most coaches) demanding their players play on a summer college team. For a lot of underclassmen getting the reps and playing time is important to win starting Spring jobs in the Fall. For a lot of programs your son will be expected to play summer ball thereby missing out on the opportunity to earn some much needed income. There is no right answer overall only what is right for you.
Good luck!