Legal Question in Family Law in Florida

Can't you restrict who he sees? He is 14 after all. You should try the "no" approach before sending him away, in my opinion. As for insurance, youe carrier will tell you. If you have custody because of a court order, you will need the court's permission to move him out of state. Consider a boarding school. A 27 year old is not really equipped to handle or parent a 14 year old.

As long as both parents agree, you can allow your 14-year-old to live with your 27-year-old. Under Florida law, no paperwork is required, though a power of attorney for school and non-emergency medical care is a good idea. Illinois law may be different, though, so you should check with a lawyer there. If your insurance company allows it, you can still keep him on your insurance. So long as you are paying child support on your 14-year-old, and so long as your 27-year-old doesn't claim him, the IRS will allow you to claim your 14-year-old as a dependent.

I agree with my colleagues however, if your 27 year old is housing this child, he can claim him as a dependent on his tax returns. You should be sure you cover this with your older child.