Sluggerdad,
Here is the perspective from a parent that had his son go the JUCO route. My guy was on the radar during HS, attending Yankee workouts in Tampa prior to his senior season opening in the Spring. He went on a Travel Ball Trip over Christmas and broke his femur. No senior year, and went undrafted even though he was still being seriously considered by the Orioles, he answered a question the wrong way (what would it take for you to sign).
At any rate, he went the JUCO route believing that once he proved he had overcome his injury he would get drafted the next season. That did not happen and he transferred to a second JUCO with better exposure. After hitting .457 he again went undrafted and was recruited to the University of Tampa where he played 2 years and had a great experience. He was drafted as a senior sign (aka no money) after UT.
He would have loved to play at the University Level for all 4 years in hindsight, he had a fair number of offers and actually decommitted to attend JUCO.
If your son is most likely to play colligate ball and then join the workforce, I would recommend going to the 4 year program that loves your son. He will likely have a wonderful college experience going that route.