I also attended a boarding school, only those who haven't been through the system will consider it a vacation home.
People often believe that if a child doesn't go through hardship he/she might turn out to be a spoilt brat but it is not entirely true. I mean I have seen those who went through severe hardship but still yet they were unable to make smart decisions about their lives.
I guess that matters is discipline just like you said, making sure a child understands life on both sides while providing for their needs.
RE: Giving Kids a different life from what we experienced