Sandiego I think you are not taking parental help into account. As I said it's not like the parents would abandon him. I even went on to say if it were me I would do the work on the house. As for rentals there Re property management companies that will handle everything from A to Z for about 10% of the rent! So he could focus on baseball just fine!
I know, you are like me, you would do everything to help your kid make the best effort. Not beefing with you, just discussing the options of this particular player.
I just think that, if I were 18 years old (and I know parents are going to give all kinds of financial advice and varying degrees of financial support), the last thing I would be thinking about is paying cash on a foreclosed property or two. Heck, at 18 if I had that kind of money in my pocket I would have been the richest person in my family and would have had 6 siblings hitting me up for everything under the sun. My parents never had $5,000 in the bank, let alone $200K. So they really could not have helped me in the same scenario...and I am sure there are instances where the same holds true every year for kids.
A couple hundred grand to a family that lives paycheck to paycheck is a lot of money...and that amount of money goes quickly (especially after taxes and advisor/agent fees). You could never have convinced me (right or wrong) that it was in my financial best interest to spend 50-70% of that amount on a house or two with the long-term plan of renovating the house and using the cash flow from renting it for my future revenue, or living in it in 4-6 years in the future. I would have just looked at it as spending all of my money on something that needed work (more money) and the cost of renting it (management). But that is just me.
I think there are some of us on here have been fortunate in life, but we all surely worked hard to get where we are. I think that every parent would want to help financially if they could...but not all can.