Don't ever be a "shoulda, coulda, woulda" guy. I should've played or I could've played or I would've played but..... People like these are a dime a dozen and are all full of regrets. In life we're going to have regrets because we will make the wrong decision but we have to realize we don't know the outcome of decisions until they are over. But you have to factor in EVERYTHING in order to make a decison even if it does turn out to be one with regrets.
If you pursue the game without ever giving up then someone will make that decision for you. College coaches may never offer you a spot on the team due to lack of ability. They may let you on the team but cut you due to lack of improvement. You may play four years and all MLB teams say you're not good enough so they don't draft you. You may get drafted and then released. I think you see where I'm going with that. If you keep going then someone is going to make the decision for you. If you make the decision yourself then you are giving up with the potential that you could have done more.
Now all that being said we can't make that decision for you. We can give you advice on what we would do or what's important to us but we will NEVER know how much fire and drive your son has in his belly. If he doesn't have the fire or drive then yes it is time to hang up the cleats and move on with life. There is no shame in that and the decision probably won't be regretful one. These are the decisions you have to make as you enter into adulthood. They are not easy and they require thinking ahead as to what the future could hold. But to make the decision to walk away you need to consider EVERYTHING to make a decision like this. I have nothing I can add to help you make this decision other than to say, consider everything.
Quick story - I was playing college baseball as a walk on at a NAIA school. I loved it and had great friends on the team although I wasn't playing. But it was frustrating not getting to play. My sophomore year I got the opportunity to be an asst. coach at a local high school under a former team mate who just graduated. He was a senior and I was his freshman backup at catcher. He got the head coaching job right out of college and wanted me to come help him. I tried to do both coach and play while going to school. Amazingly my grades started plummeting and I had make a decision on what to do.
I decided to give up playing and focusing on coaching. I knew my future was in coaching although I had no idea how good I would be. So I went to coach and told him I was done, thanked him for the opportunity to walk on and be part of the team but I had to start planning for the future. Coach was awesome about it and understood.
I started coaching and we had some success. I started building a name for myself. After four years at the school there were some changes and I was no longer coaching there. That summer another former team mate of mine from college was named head coach at another local school and asked me to coach for him. But I also had two other offers from other schools that were fairly close to the second school. I felt pretty good about where I was going with my coaching career. I only coached at that school one year and we made it to the final 8 teams in the state. The next year I got a full time teaching job about 8 hours from the two schools I started at. My second year they named me head coach. The next 9 years saw my teams set school record after record and we had more success than any other team in the school's history. After that I decided I wanted to make a change and be closer to some family and moved to NC. For the past three years I've been an asst. at a very successful school. We've won our conference every year and were state runners up. This past June we had a kid drafted by the Yankees.
The good Lord truly has blessed my coaching career so far and I hope He continues to bless it even more. I've made so many friends and helped to influence so many kids and accomplished so much. But I'm a "shoulda, coulda, woulda" person.
I made the right decision to give up playing and focusing on my teaching / coaching career. I wouldn't trade the wonderful things I've been able to experience while coaching for anything in this world.......but I truly miss playing the game and I do sometimes wish I continued to play the last two years of college. Looking back now I know I never would have went past college and I was lucky just to get to play college. I gave up those last two years to do something good with my life but there are times it gnaws at me.
Nobody here can really tell you anything to help you make that decision. It's all on the player and it's not something to take lightly. Please consider everything and make a decision you can live with.
I wish your son the absolute and very best in making the right decision for him.